The Vespiary

The Hive => Methods Discourse => Topic started by: Aurelius on May 19, 2004, 07:29:00 PM

Title: Synthesis of Benzaldehydes
Post by: Aurelius on May 19, 2004, 07:29:00 PM
Synthesis of Benzaldehyde and it Substituted Analogues

Benzaldehyde Derived:

Benzaldehyde:

Post 511939 (https://www.thevespiary.org/talk/index.php?topic=11133.msg51193900#msg51193900)

(Kinetic: "Cinnamic acid to benzaldehyde", Newbee Forum)

Post 208719 (https://www.thevespiary.org/talk/index.php?topic=7285.msg20871900#msg20871900)

(Osmium: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)

Patents Related To Link Above:

Post 208782 (https://www.thevespiary.org/talk/index.php?topic=7285.msg20878200#msg20878200)

(PolytheneSam: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)


Post 377691 (https://www.thevespiary.org/talk/index.php?topic=9842.msg37769100#msg37769100)

(moo: "Aldehydes from Grignard reagents with formic acid", Methods Discourse)

Post 241349 (https://www.thevespiary.org/talk/index.php?topic=7285.msg24134900#msg24134900)

(foxy2: "benzaldehyde from toluene - Additions", Chemistry Discourse)

Post 244957 (https://www.thevespiary.org/talk/index.php?topic=11766.msg24495700#msg24495700)

(Chemikaze: "Benzaldehyde via MnO2 oxidation of toluene", Novel Discourse)

Related:

Post 296395 (missing)

(hest: "You need 'activated' MnO2.", Newbee Forum)

or

https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxycodone.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxycodone.html)



Post 354314 (https://www.thevespiary.org/talk/index.php?topic=7285.msg35431400#msg35431400)

(Rhodium: "General Method for the Preparation of ...", Chemistry Discourse)
(from benzyl alcohol)

Post 479722 (https://www.thevespiary.org/talk/index.php?topic=7285.msg47972200#msg47972200)

(lugh: "Reference Uploaded", Chemistry Discourse)
(Deox. of Benzoic acid)

Post 493837 (https://www.thevespiary.org/talk/index.php?topic=7285.msg49383700#msg49383700)

(moo: "Benzoic acid to benzaldehyde or benzene", Chemistry Discourse)
(second part of deox.)

Refs for Various Methods:

Post 354361 (https://www.thevespiary.org/talk/index.php?topic=7285.msg35436100#msg35436100)

(GC_MS: "Meyer", Chemistry Discourse)


Post 444540 (missing)

(Lego: "Solventless oxidation with KMnO4/montmorillonite", Chemistry Discourse)
(tol. to benz.)

Post 459026 (https://www.thevespiary.org/talk/index.php?topic=7285.msg45902600#msg45902600)

(hermanroempp: "Just another oxidiser - Manganese-(III)-sulfate", Chemistry Discourse)
(tol. to benz.)

Post 468094 (https://www.thevespiary.org/talk/index.php?topic=7285.msg46809400#msg46809400)

(moo: "I've thought about the possibility of ...", Chemistry Discourse)
(tol. to benz.)

Post 498021 (https://www.thevespiary.org/talk/index.php?topic=7285.msg49802100#msg49802100)

(Organikum: "H2O2 toluene oxidation (vanadium catalyzed)", Chemistry Discourse)
(tol. to benz.)

Post 473147 (https://www.thevespiary.org/talk/index.php?topic=7285.msg47314700#msg47314700)

(Rhodium: "Toluene to Benzaldehyde using Co(II)-Peroxygen", Chemistry Discourse)

Post 457354 (https://www.thevespiary.org/talk/index.php?topic=7285.msg45735400#msg45735400)

(LaBTop: "Crossposting, Hah!", Chemistry Discourse)
(tol. to benz. by air ox.)

Post 471369 (https://www.thevespiary.org/talk/index.php?topic=7285.msg47136900#msg47136900)

(halfkast: "Chomic", Chemistry Discourse)
(tol. to benz. by air ox.)

http://www.sciencemadness.org/papers/toluene_air_oxidation.pdf (http://www.sciencemadness.org/papers/toluene_air_oxidation.pdf)


http://www.sciencemadness.org/papers/toluene_air_oxidation2.pdf (http://www.sciencemadness.org/papers/toluene_air_oxidation2.pdf)



Post 479888 (https://www.thevespiary.org/talk/index.php?topic=7285.msg47988800#msg47988800)

(Rhodium: "More on Toluene -> Benzaldehyde", Chemistry Discourse)


Post 458012 (https://www.thevespiary.org/talk/index.php?topic=7285.msg45801200#msg45801200)

(Tdurden969: "References", Chemistry Discourse)
(electro. to benz.)

Post 493948 (https://www.thevespiary.org/talk/index.php?topic=7285.msg49394800#msg49394800)

(Organikum: "Benzoic acid to benzaldehyde by electrolysis", Chemistry Discourse)
(benz. acid. electro.)

Post 437235 (missing)

(Organikum: "B-dehyde", Stimulants)
(patents)


Mono-Substituted Benzaldehydes:
Salicylaldehyde: 2-OH-

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)
(see Ref # 11)

Post 422019 (https://www.thevespiary.org/talk/index.php?topic=8836.msg42201900#msg42201900)

(Vitus_Verdegast: "found an interesting article", Methods Discourse)


Anisaldeyde: 4-MeO

Post 382264 (https://www.thevespiary.org/talk/index.php?topic=11385.msg38226400#msg38226400)

(Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)

Post 475637 (https://www.thevespiary.org/talk/index.php?topic=11874.msg47563700#msg47563700)

(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)


Post 504013 (https://www.thevespiary.org/talk/index.php?topic=7516.msg50401300#msg50401300)

(starlight: "some interesting mandelic acid patents", Chemistry Discourse)

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)
(see ref #11)

Di-Substituted Benzaldehydes:
2-OH-3-BuO-

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-3-t-Amyl-

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-4-Me-

Post 234191 (missing)

(megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)


2-OH-5-Br: (5-BromoSalicylaldehyde)

Post 511284 (https://www.thevespiary.org/talk/index.php?topic=6626.msg51128400#msg51128400)

(lugh: "5-bromosalicylaldehyde", Chemistry Discourse)


2-OH-5-Me-

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-5-MeO-

Post 214710 (https://www.thevespiary.org/talk/index.php?topic=6692.msg21471000#msg21471000)

(Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)

Post 511008 (https://www.thevespiary.org/talk/index.php?topic=6626.msg51100800#msg51100800)

(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)


2,5-DiEtO-

Post 239307 (https://www.thevespiary.org/talk/index.php?topic=11917.msg23930700#msg23930700)

(Rhodium: "Re: Syringaldehyde via Duff formylation", Novel Discourse)


2-OH-5-MeO-

Post 290438 (https://www.thevespiary.org/talk/index.php?topic=6360.msg29043800#msg29043800)

(Lilienthal: "2-hydroxy-5-MeO-BA: The easy way", Chemistry Discourse)

Post 234191 (missing)

(megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)

Post 475637 (https://www.thevespiary.org/talk/index.php?topic=11874.msg47563700#msg47563700)

(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)

Post 330714 (https://www.thevespiary.org/talk/index.php?topic=7674.msg33071400#msg33071400)

(Antoncho: "A patented improvement", Chemistry Discourse)


2-OH-6-Me-

Post 234191 (missing)

(megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)


2,5-DiMeO-
Post 510729 (not existing)

Post 493429 (https://www.thevespiary.org/talk/index.php?topic=9163.msg49342900#msg49342900)

(Nicodem: "HCHO/Mg(II) formylation + methylation patent", Methods Discourse)

Post 348592 (https://www.thevespiary.org/talk/index.php?topic=7674.msg34859200#msg34859200)

(Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)

Post 423268 (https://www.thevespiary.org/talk/index.php?topic=7432.msg42326800#msg42326800)

(foxy2: "Synthesis of 2,5-dimethoxybenzaldehyde", Chemistry Discourse)

Post 473079 (https://www.thevespiary.org/talk/index.php?topic=12074.msg47307900#msg47307900)

(Rhodium: "Gattermann 2,5-Dimethoxybenzaldehyde", Novel Discourse)

Post 454518 (https://www.thevespiary.org/talk/index.php?topic=7432.msg45451800#msg45451800)

(Rhodium: "Two Syntheses of 2,5-Dimethoxybenzaldehyde", Chemistry Discourse)

Post 475637 (https://www.thevespiary.org/talk/index.php?topic=11874.msg47563700#msg47563700)

(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)

Post 214710 (https://www.thevespiary.org/talk/index.php?topic=6692.msg21471000#msg21471000)

(Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)


The following procedure is NOT valid:

Post 70528 (https://www.thevespiary.org/talk/index.php?topic=12361.msg7052800#msg7052800)

(karel: "Synth of 2,5-dimethoxybenzaldehyde", Serious Chemistry)
(must also read

Post 299121 (https://www.thevespiary.org/talk/index.php?topic=6905.msg29912100#msg29912100)

(karel: "Revision of post 70528", Chemistry Discourse)
)

Veratraldehyde: 3,4-DiMeO-

http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0619 (http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0619)




Protocatechualdehyde: 3,4-DiOH-

Post 477628 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47762800#msg47762800)

(Rhodium: "Vanillin to Protocatechualdehyde (AlCl3/Py)", Methods Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html)



Bourbonal: 3-EtO-4-OH-

3,5-DiMeO-

Post 473076 (https://www.thevespiary.org/talk/index.php?topic=7285.msg47307600#msg47307600)

(Rhodium: "Benzoic Acids to Benzaldehydes", Chemistry Discourse)


Vanillin: 4-OH-3-MeO-

Post 275285 (https://www.thevespiary.org/talk/index.php?topic=6626.msg27528500#msg27528500)

(foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse)
(or the direct link below)

http://valhalla.chem.udel.edu/vanillin.html (http://valhalla.chem.udel.edu/vanillin.html)


Post 286983 (https://www.thevespiary.org/talk/index.php?topic=6626.msg28698300#msg28698300)

(foxy2: "Hmmm,  CO2????", Chemistry Discourse)

Post 504013 (https://www.thevespiary.org/talk/index.php?topic=7516.msg50401300#msg50401300)

(starlight: "some interesting mandelic acid patents", Chemistry Discourse)

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)
(see ref # 11)

Post 211048 (missing)

(Rhodium: "Re: Vanillin from OTC Vanilla Extract", Chemistry Discourse)

Post 511008 (https://www.thevespiary.org/talk/index.php?topic=6626.msg51100800#msg51100800)

(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)


3-Alkoxy-4-OH-

Post 504013 (https://www.thevespiary.org/talk/index.php?topic=7516.msg50401300#msg50401300)

(starlight: "some interesting mandelic acid patents", Chemistry Discourse)


4-EtO-3-MeO-

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)



Tri-Substituted Benzaldehydes:
2-Bromo-3,4-DiMeO-

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)

Post 214376 (missing)

(foxy2: "Re: 2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse)


2-OH-3,5-DiBr

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-3,5-Di-t-Bu- (also: 3,5-Di-t-Bu-Salicylaldehyde)

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-3-Cl-5-t-Bu 

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2-OH-3-Me-5-t-Amyl

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2,3,5-TriMeO-

Post 494386 (https://www.thevespiary.org/talk/index.php?topic=11422.msg49438600#msg49438600)

(Rhodium: "Synthesis of TMA-2 Precursors from Vanillin", Novel Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)



2-OH-3-MeO-5-Me-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


2-BromoVanillin: 2-Br-3-MeO-4-OH-

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)


2-Br-4,5-DiMeO-

Post 214369 (missing)

(foxy2: "2 Bromination of 3,4-dimethoxybenzaldehyde", Chemistry Discourse)


Asarylaldehyde: 2,4,5-TriMeO-

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)


Post 471601 (https://www.thevespiary.org/talk/index.php?topic=9605.msg47160100#msg47160100)

(Rhodium: "Indirect 6-Methoxylation of Veratraldehyde", Methods Discourse)


2,4,6-TriMeO-

Post 480958 (https://www.thevespiary.org/talk/index.php?topic=7668.msg48095800#msg48095800)

(hest: "Synt of 2,4,6-trimethoxybenzaldehyde", Chemistry Discourse)

Post 481038 (https://www.thevespiary.org/talk/index.php?topic=7668.msg48103800#msg48103800)

(Rhodium: "Synthesis of 2,4,6-Trimethoxybenzaldehyde", Chemistry Discourse)


2,5-DiMeO-3-Me-

Post 300201 (https://www.thevespiary.org/talk/index.php?topic=11887.msg30020100#msg30020100)

(Antoncho: "3-methyl-2,5-diMeO-benzaldehyde", Novel Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html)



2,5-DiMeO-4-Me-

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html)



3,4-DiMeO-5-OH-

Post 506221 (https://www.thevespiary.org/talk/index.php?topic=7389.msg50622100#msg50622100)

(Mephisto: "Synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde", Chemistry Discourse)


3,4,5-TriMeO-

Post 501059 (https://www.thevespiary.org/talk/index.php?topic=9506.msg50105900#msg50105900)

(ning: "TRANSLATED: Chinese 3,4,5 TMB article", Methods Discourse)

Post 507150 (https://www.thevespiary.org/talk/index.php?topic=9506.msg50715000#msg50715000)

(Rhodium: "3,4,5-Trimethoxybenzaldehyde from Gallic Acid", Methods Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html)


https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)



3,4,6-TriMeO-

Post 464340 (https://www.thevespiary.org/talk/index.php?topic=12217.msg46434000#msg46434000)

(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)


6-BromoVanillin: 3-MeO-4-OH-6-Br-

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)


3-DiMe-2-OH-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


3,5-Bis(DiMeAminoMe)-2-OH-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


3,5-DiBr-4-OH-

Post 275643 (https://www.thevespiary.org/talk/index.php?topic=6626.msg27564300#msg27564300)

(Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)


3,5-DiMe-4-OH-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


3,5-DiMeO-4-OH-

Post 275269 (https://www.thevespiary.org/talk/index.php?topic=6626.msg27526900#msg27526900)

(Antoncho: "Re: Vanillin", Chemistry Discourse)


3,5-Bis(DiMeAminoMe)-4-OH-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


3,5-Di-t-Bu-4-OH-

Post 208298 (missing)

(Antoncho: "Duff formylation in aq. AcOH - 90% yield :))", Chemistry Discourse)


4-I-2,5-DiMeO-

Post 422838 (https://www.thevespiary.org/talk/index.php?topic=9768.msg42283800#msg42283800)

(GC_MS: "1-(4-iodo-2,5-dimethoxyphenyl)-2-propanone", Methods Discourse)

Post 469528 (https://www.thevespiary.org/talk/index.php?topic=9768.msg46952800#msg46952800)

(Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse)


4-Cl-2,5-DiMeO-

Post 106232 (https://www.thevespiary.org/talk/index.php?topic=6431.msg10623200#msg10623200)

(rev drone: "Re: Iodination via NIS -- various conditions", Chemistry Discourse)

Post 482940 (https://www.thevespiary.org/talk/index.php?topic=6431.msg48294000#msg48294000)

(Lego: "Duff formylation of 2-chloro-1,4-dimethoxybenzene", Chemistry Discourse)


4-Br-2,5-DiMeO-

Post 106232 (https://www.thevespiary.org/talk/index.php?topic=6431.msg10623200#msg10623200)

(rev drone: "Re: Iodination via NIS -- various conditions", Chemistry Discourse)

Post 469528 (https://www.thevespiary.org/talk/index.php?topic=9768.msg46952800#msg46952800)

(Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse)

Post 468077 (missing)

(moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse)

Post 468078 (missing)

(moo: "Oxidations and brominations w/ H2O2/Br2/HBr", Methods Discourse)


5-NO2-2,3-DiMeO-

Post 425432 (https://www.thevespiary.org/talk/index.php?topic=8836.msg42543200#msg42543200)

(Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)


5-NO2-2-MeO-3-EtO-

Post 425432 (https://www.thevespiary.org/talk/index.php?topic=8836.msg42543200#msg42543200)

(Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)


Syringaldehyde: 4-OH-3,5-DiMeO-

Post 355336 (https://www.thevespiary.org/talk/index.php?topic=11385.msg35533600#msg35533600)

(Antoncho: "Another EXCELLENT formylation!", Novel Discourse)

Post 275285 (https://www.thevespiary.org/talk/index.php?topic=6626.msg27528500#msg27528500)

(foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html)


Post 275643 (https://www.thevespiary.org/talk/index.php?topic=6626.msg27564300#msg27564300)

(Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)

Post 286983 (https://www.thevespiary.org/talk/index.php?topic=6626.msg28698300#msg28698300)

(foxy2: "Hmmm,  CO2????", Chemistry Discourse)

Post 235806 (missing)

(Osmium: "Re: Magnesium Alkoxides", Chemistry Discourse)
(as seen in

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html)

)

Post 239082 (https://www.thevespiary.org/talk/index.php?topic=11917.msg23908200#msg23908200)

(Antoncho: "Syringaldehyde via Duff formylation", Novel Discourse)

Post 511008 (https://www.thevespiary.org/talk/index.php?topic=6626.msg51100800#msg51100800)

(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)


4-OH-5-MeO-3-Me-  (aka: 5-Me-Vanillin)

Post 253386 (https://www.thevespiary.org/talk/index.php?topic=11797.msg25338600#msg25338600)

(slothrop: "5-Methyl-MDA", Novel Discourse)


4-OH-5-Me-3-MeO-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


4,5-DiOH-3-Me-

Post 253386 (https://www.thevespiary.org/talk/index.php?topic=11797.msg25338600#msg25338600)

(slothrop: "5-Methyl-MDA", Novel Discourse)


5-DiMeAminoMe-2-OH-3-MeO-

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


5-Bromo-3-DiMeo-

Post 474077 (https://www.thevespiary.org/talk/index.php?topic=8829.msg47407700#msg47407700)

(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)


5-DiMeAminoMe-4-OH-3-MeO-

Post 253386 (https://www.thevespiary.org/talk/index.php?topic=11797.msg25338600#msg25338600)

(slothrop: "5-Methyl-MDA", Novel Discourse)

Post 486611 (https://www.thevespiary.org/talk/index.php?topic=11797.msg48661100#msg48661100)

(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)


Higher-Poly-Substituted Benzaldehydes:
2-OH-3-i-Pro-5-Cl-6-Me-

Post 355308 (https://www.thevespiary.org/talk/index.php?topic=11917.msg35530800#msg35530800)

(foxy2: "More Duff Reaction", Novel Discourse)


2,5-DiMeO-3,6-DiMe-

Post 472752 (https://www.thevespiary.org/talk/index.php?topic=12074.msg47275200#msg47275200)

(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)


2,3,4-TriMeO-3,6-DiMe-

Post 472752 (https://www.thevespiary.org/talk/index.php?topic=12074.msg47275200#msg47275200)

(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)


2,4,5-TriMeO-3,6-DiMe-

Post 472752 (https://www.thevespiary.org/talk/index.php?topic=12074.msg47275200#msg47275200)

(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)


4-OH-2,5-DiMeo-3,6-DiMe-

Post 472752 (https://www.thevespiary.org/talk/index.php?topic=12074.msg47275200#msg47275200)

(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)


Piperonal Derived:

Piperonal (Heliotropine): 3,4-MD-Benz.

Post 463350 (https://www.thevespiary.org/talk/index.php?topic=11504.msg46335000#msg46335000)

(Antoncho: "A great piperonal patent", Novel Discourse)

Post 391475 (https://www.thevespiary.org/talk/index.php?topic=12187.msg39147500#msg39147500)

(pHarmacist: "One More piperonal patent, High-yielding", Novel Discourse)

Post 328397 (https://www.thevespiary.org/talk/index.php?topic=12187.msg32839700#msg32839700)

(demorol: "Piperonal synthesis", Novel Discourse)

Post 329015 (https://www.thevespiary.org/talk/index.php?topic=12187.msg32901500#msg32901500)

(demorol: "More patents", Novel Discourse)

Post 382264 (https://www.thevespiary.org/talk/index.php?topic=11385.msg38226400#msg38226400)

(Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)


5-OH-

Post 504409 (https://www.thevespiary.org/talk/index.php?topic=12217.msg50440900#msg50440900)

(Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)

Also:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html)



5-Br-

Post 507151 (https://www.thevespiary.org/talk/index.php?topic=9383.msg50715100#msg50715100)

(Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)


5-Me-

Post 253386 (https://www.thevespiary.org/talk/index.php?topic=11797.msg25338600#msg25338600)

(slothrop: "5-Methyl-MDA", Novel Discourse)


6-OH-

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


6-NH2-

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


6-NO2-

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


2-Br-6-MeO-

Post 507151 (https://www.thevespiary.org/talk/index.php?topic=9383.msg50715100#msg50715100)

(Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)


1-MeO-2,3-MD-

Post 484717 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48471700#msg48471700)

(Rhodium: "Croweacinaldehyde  & Isomers", Novel Discourse)


2,3-MD-4-MeO-

Post 464340 (https://www.thevespiary.org/talk/index.php?topic=12217.msg46434000#msg46434000)

(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)

Post 484717 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48471700#msg48471700)

(Rhodium: "Croweacinaldehyde  & Isomers", Novel Discourse)


Croweacinaldehyde: 2-MeO-3,4-MD-

Post 484271 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48427100#msg48427100)

(Rhodium: "Croweacinaldehyde from Pyrogallol (55%)", Novel Discourse)

Post 484720 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48472000#msg48472000)

(Rhodium: "Croweacinaldehyde", Novel Discourse)

Post 464340 (https://www.thevespiary.org/talk/index.php?topic=12217.msg46434000#msg46434000)

(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)

Post 245205 (missing)

(Rhodium: "Re: Benzaldehyde Of Croweacin?", Chemistry Discourse)

Post 484717 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48471700#msg48471700)

(Rhodium: "Croweacinaldehyde  & Isomers", Novel Discourse)


2-Alkoxy-4,5-MD-

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


Carpacinaldehyde: 2-MeO-4,5-MD-

Post 247833 (missing)

(Rhodium: "Carpacin isolation & Physical Data", Chemistry Discourse)

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


Apiolaldehyde: 2,5-DiMeO-3,4-MD-

Post 489559 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48955900#msg48955900)

(Rhodium: "Synthesis of Myristicinaldehyde/Apiolealdehyde", Novel Discourse)

https://www.thevespiary.org/rhodium/Rhodium/chemistry/myristicinaldehyde.shulgin.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/myristicinaldehyde.shulgin.html)



Myristicinaldehyde: 3-MeO-3,4-MD-

Post 509800 (https://www.thevespiary.org/talk/index.php?topic=12217.msg50980000#msg50980000)

(Rhodium: "Myristicin Derivatives", Novel Discourse)

Post 508799 (https://www.thevespiary.org/talk/index.php?topic=11504.msg50879900#msg50879900)

(Wraith: "Methylenation without KF or PTC", Novel Discourse)

Post 504409 (https://www.thevespiary.org/talk/index.php?topic=12217.msg50440900#msg50440900)

(Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)

Also:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html)


Post 489659 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48965900#msg48965900)

(Rhodium: "Myristicin & Myristicinaldehyde", Novel Discourse)

IR of Myristicin

Post 494937 (https://www.thevespiary.org/talk/index.php?topic=12528.msg49493700#msg49493700)

(Islamybad: "Here's the IR spectrum of myristicin from two...", Serious Chemistry)

Post 452949 (https://www.thevespiary.org/talk/index.php?topic=7255.msg45294900#msg45294900)

(GC_MS: "myristicinaldehyde", Chemistry Discourse)
(see warning below before attempting this synthesis:)

Warning about TetraNitroMethane and Relatives:

Post 355957 (https://www.thevespiary.org/talk/index.php?topic=7597.msg35595700#msg35595700)

(GC_MS: "How dangerous is tetranitromethane?", Chemistry Discourse)


3,4-MD-6-OH-

Post 464339 (https://www.thevespiary.org/talk/index.php?topic=11785.msg46433900#msg46433900)

(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)


6-OH-2-MeO-3,4-MD-

Post 484717 (https://www.thevespiary.org/talk/index.php?topic=12217.msg48471700#msg48471700)

(Rhodium: "Croweacinaldehyde  & Isomers", Novel Discourse)


General Aldehyde Synthesis or those containing large numbers of aldehyde products:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/formylations.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/formylations.html)


Post 355321 (https://www.thevespiary.org/talk/index.php?topic=11385.msg35532100#msg35532100)

(foxy2: "formylation by the "nitroso" method", Novel Discourse)

Post 355336 (https://www.thevespiary.org/talk/index.php?topic=11385.msg35533600#msg35533600)

(Antoncho: "Another EXCELLENT formylation!", Novel Discourse)

Post 235460 (missing)

(Antoncho: "Re: Formylations", Chemistry Discourse)

Post 422033 (https://www.thevespiary.org/talk/index.php?topic=8836.msg42203300#msg42203300)

(Vitus_Verdegast: "R-T articles that might be interesting", Methods Discourse)

https://www.thevespiary.org/rhodium/Rhodium/pdf/bromo2hydroxy-benzaldehydes.pdf (https://www.thevespiary.org/rhodium/Rhodium/pdf/bromo2hydroxy-benzaldehydes.pdf)



Side Notes:
Formylation Mechanism:

Post 481046 (https://www.thevespiary.org/talk/index.php?topic=9163.msg48104600#msg48104600)

(Rhodium: "Magnesium ortho-Formylation Mechanism", Methods Discourse)
:)

Several Naturally Occuring Aldehydes:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html)