Synthesis of Benzaldehyde and it Substituted AnaloguesBenzaldehyde Derived:Benzaldehyde:Post 511939
(Kinetic: "Cinnamic acid to benzaldehyde", Newbee Forum)Post 208719
(Osmium: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)Patents Related To Link Above:
Post 208782
(PolytheneSam: "Re: The easiest synth of benzaldehyde from toluene", Chemistry Discourse)Post 377691
(moo: "Aldehydes from Grignard reagents with formic acid", Methods Discourse)Post 241349
(foxy2: "benzaldehyde from toluene - Additions", Chemistry Discourse)Post 244957
(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
Post 354314
(Rhodium: "General Method for the Preparation of ...", Chemistry Discourse) (from benzyl alcohol)
Post 479722
(lugh: "Reference Uploaded", Chemistry Discourse) (Deox. of Benzoic acid)
Post 493837
(moo: "Benzoic acid to benzaldehyde or benzene", Chemistry Discourse) (second part of deox.)
Refs for Various Methods:
Post 354361
(GC_MS: "Meyer", Chemistry Discourse)Post 444540 (missing)
(Lego: "Solventless oxidation with KMnO4/montmorillonite", Chemistry Discourse) (tol. to benz.)
Post 459026
(hermanroempp: "Just another oxidiser - Manganese-(III)-sulfate", Chemistry Discourse) (tol. to benz.)
Post 468094
(moo: "I've thought about the possibility of ...", Chemistry Discourse) (tol. to benz.)
Post 498021
(Organikum: "H2O2 toluene oxidation (vanadium catalyzed)", Chemistry Discourse) (tol. to benz.)
Post 473147
(Rhodium: "Toluene to Benzaldehyde using Co(II)-Peroxygen", Chemistry Discourse)Post 457354
(LaBTop: "Crossposting, Hah!", Chemistry Discourse) (tol. to benz. by air ox.)
Post 471369
(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_oxidation2.pdf
Post 479888
(Rhodium: "More on Toluene -> Benzaldehyde", Chemistry Discourse)Post 458012
(Tdurden969: "References", Chemistry Discourse) (electro. to benz.)
Post 493948
(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
(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see Ref # 11)
Post 422019
(Vitus_Verdegast: "found an interesting article", Methods Discourse)Anisaldeyde: 4-MeOPost 382264
(Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)Post 475637
(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
Post 504013
(starlight: "some interesting mandelic acid patents", Chemistry Discourse)Post 474077
(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse) (see ref #11)
Di-Substituted Benzaldehydes:2-OH-3-BuO-Post 355308
(foxy2: "More Duff Reaction", Novel Discourse)2-OH-3-t-Amyl-Post 355308
(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
(lugh: "5-bromosalicylaldehyde", Chemistry Discourse)2-OH-5-Me-Post 355308
(foxy2: "More Duff Reaction", Novel Discourse)2-OH-5-MeO-Post 214710
(Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)Post 511008
(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)2,5-DiEtO-Post 239307
(Rhodium: "Re: Syringaldehyde via Duff formylation", Novel Discourse)2-OH-5-MeO-Post 290438
(Lilienthal: "2-hydroxy-5-MeO-BA: The easy way", Chemistry Discourse)Post 234191 (missing)
(megamole: "Re: Magnesium Alkoxides", Chemistry Discourse)Post 475637
(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)Post 330714
(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
(Nicodem: "HCHO/Mg(II) formylation + methylation patent", Methods Discourse)Post 348592
(Antoncho: "Methyl iodide methylation of 2-OH-5-MeO-BA.", Chemistry Discourse)Post 423268
(foxy2: "Synthesis of 2,5-dimethoxybenzaldehyde", Chemistry Discourse)Post 473079
(Rhodium: "Gattermann 2,5-Dimethoxybenzaldehyde", Novel Discourse)Post 454518
(Rhodium: "Two Syntheses of 2,5-Dimethoxybenzaldehyde", Chemistry Discourse)Post 475637
(Rhodium: "Synthesis of 2C-B from Anise Oil (Anethole)", Novel Discourse)Post 214710
(Karl: "2-Hydroxy-5-methoxybenzaldehyde", Chemistry Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
The following procedure is NOT valid:Post 70528
(karel: "Synth of 2,5-dimethoxybenzaldehyde", Serious Chemistry) (must also read
Post 299121
(karel: "Revision of post 70528", Chemistry Discourse))
Veratraldehyde: 3,4-DiMeO-http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0619
Protocatechualdehyde: 3,4-DiOH-Post 477628
(Rhodium: "Vanillin to Protocatechualdehyde (AlCl3/Py)", Methods Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html
Bourbonal: 3-EtO-4-OH-3,5-DiMeO-Post 473076
(Rhodium: "Benzoic Acids to Benzaldehydes", Chemistry Discourse)Vanillin: 4-OH-3-MeO-Post 275285
(foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse) (or the direct link below)
http://valhalla.chem.udel.edu/vanillin.html
Post 286983
(foxy2: "Hmmm, CO2?
", Chemistry Discourse)Post 504013
(starlight: "some interesting mandelic acid patents", Chemistry Discourse)Post 474077
(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
(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)3-Alkoxy-4-OH-Post 504013
(starlight: "some interesting mandelic acid patents", Chemistry Discourse)4-EtO-3-MeO-https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
Tri-Substituted Benzaldehydes:2-Bromo-3,4-DiMeO-Post 474077
(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-DiBrPost 355308
(foxy2: "More Duff Reaction", Novel Discourse)2-OH-3,5-Di-t-Bu- (also: 3,5-Di-t-Bu-Salicylaldehyde)Post 355308
(foxy2: "More Duff Reaction", Novel Discourse)2-OH-3-Cl-5-t-Bu Post 355308
(foxy2: "More Duff Reaction", Novel Discourse)2-OH-3-Me-5-t-AmylPost 355308
(foxy2: "More Duff Reaction", Novel Discourse)2,3,5-TriMeO-Post 494386
(Rhodium: "Synthesis of TMA-2 Precursors from Vanillin", Novel Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
2-OH-3-MeO-5-Me-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)2-BromoVanillin: 2-Br-3-MeO-4-OH-Post 474077
(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
Post 471601
(Rhodium: "Indirect 6-Methoxylation of Veratraldehyde", Methods Discourse)2,4,6-TriMeO-Post 480958
(hest: "Synt of 2,4,6-trimethoxybenzaldehyde", Chemistry Discourse)Post 481038
(Rhodium: "Synthesis of 2,4,6-Trimethoxybenzaldehyde", Chemistry Discourse)2,5-DiMeO-3-Me-Post 300201
(Antoncho: "3-methyl-2,5-diMeO-benzaldehyde", Novel Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html
2,5-DiMeO-4-Me-https://www.thevespiary.org/rhodium/Rhodium/chemistry/methyldimethoxybenzaldehydes.html
3,4-DiMeO-5-OH-Post 506221
(Mephisto: "Synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde", Chemistry Discourse)3,4,5-TriMeO-Post 501059
(ning: "TRANSLATED: Chinese 3,4,5 TMB article", Methods Discourse)Post 507150
(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/me3po4.html
3,4,6-TriMeO-Post 464340
(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)6-BromoVanillin: 3-MeO-4-OH-6-Br-Post 474077
(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)3-DiMe-2-OH-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)3,5-Bis(DiMeAminoMe)-2-OH-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)3,5-DiBr-4-OH-Post 275643
(Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)3,5-DiMe-4-OH-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)3,5-DiMeO-4-OH-Post 275269
(Antoncho: "Re: Vanillin", Chemistry Discourse)3,5-Bis(DiMeAminoMe)-4-OH-Post 486611
(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
(GC_MS: "1-(4-iodo-2,5-dimethoxyphenyl)-2-propanone", Methods Discourse)Post 469528
(Chimimanie: "halogenation of 2,5-DMB & benzonitrile + DOI ?", Methods Discourse)4-Cl-2,5-DiMeO-Post 106232
(rev drone: "Re: Iodination via NIS -- various conditions", Chemistry Discourse)Post 482940
(Lego: "Duff formylation of 2-chloro-1,4-dimethoxybenzene", Chemistry Discourse)4-Br-2,5-DiMeO-Post 106232
(rev drone: "Re: Iodination via NIS -- various conditions", Chemistry Discourse)Post 469528
(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
(Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)5-NO2-2-MeO-3-EtO-Post 425432
(Vitus_Verdegast: "J. Chem. Soc. (1923) 123, page 1587 and 1588", Methods Discourse)Syringaldehyde: 4-OH-3,5-DiMeO-Post 355336
(Antoncho: "Another EXCELLENT formylation!", Novel Discourse)Post 275285
(foxy2: "5-Br-Vanillin Methoxylation (CuBr/EtOAc/NaOMe)", Chemistry Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/345-tmb.html
Post 275643
(Antoncho: "Syringaldehyde from p-cresol in two steps", Chemistry Discourse)Post 286983
(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
)
Post 239082
(Antoncho: "Syringaldehyde via Duff formylation", Novel Discourse)Post 511008
(demorol: "Methoxylation of various aryl bromides", Chemistry Discourse)4-OH-5-MeO-3-Me- (aka: 5-Me-Vanillin)Post 253386
(slothrop: "5-Methyl-MDA", Novel Discourse)4-OH-5-Me-3-MeO-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)4,5-DiOH-3-Me-Post 253386
(slothrop: "5-Methyl-MDA", Novel Discourse)5-DiMeAminoMe-2-OH-3-MeO-Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)5-Bromo-3-DiMeo-Post 474077
(Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)5-DiMeAminoMe-4-OH-3-MeO-Post 253386
(slothrop: "5-Methyl-MDA", Novel Discourse)Post 486611
(Rhodium: "Reference #5: C-Methylation of Vanillin", Novel Discourse)Higher-Poly-Substituted Benzaldehydes:2-OH-3-i-Pro-5-Cl-6-Me-Post 355308
(foxy2: "More Duff Reaction", Novel Discourse)2,5-DiMeO-3,6-DiMe-Post 472752
(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)2,3,4-TriMeO-3,6-DiMe-Post 472752
(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)2,4,5-TriMeO-3,6-DiMe-Post 472752
(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)4-OH-2,5-DiMeo-3,6-DiMe-Post 472752
(Manichi: "Methylated PEA benzaldehyde precursors", Novel Discourse)Piperonal Derived:Piperonal (Heliotropine): 3,4-MD-Benz.Post 463350
(Antoncho: "A great piperonal patent", Novel Discourse)Post 391475
(pHarmacist: "One More piperonal patent, High-yielding", Novel Discourse)Post 328397
(demorol: "Piperonal synthesis", Novel Discourse)Post 329015
(demorol: "More patents", Novel Discourse)Post 382264
(Antoncho: "Zealot: azomethinic (Haack) formylation", Novel Discourse)5-OH-Post 504409
(Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)Also:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html
5-Br-Post 507151
(Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)5-Me-Post 253386
(slothrop: "5-Methyl-MDA", Novel Discourse)6-OH-Post 464339
(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)6-NH2-Post 464339
(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)6-NO2-Post 464339
(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)2-Br-6-MeO-Post 507151
(Rhodium: "Synthesis of 5-Bromopiperonal", Methods Discourse)1-MeO-2,3-MD-Post 484717
(Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)2,3-MD-4-MeO-Post 464340
(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)Post 484717
(Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)Croweacinaldehyde: 2-MeO-3,4-MD-Post 484271
(Rhodium: "Croweacinaldehyde from Pyrogallol (55%)", Novel Discourse)Post 484720
(Rhodium: "Croweacinaldehyde", Novel Discourse)Post 464340
(imp: "Synthesis of MMDA-3a and MMDA-3b Benzaldehydes", Novel Discourse)Post 245205 (missing)
(Rhodium: "Re: Benzaldehyde Of Croweacin?", Chemistry Discourse)Post 484717
(Rhodium: "Croweacinaldehyde & Isomers", Novel Discourse)2-Alkoxy-4,5-MD-Post 464339
(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
(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)Apiolaldehyde: 2,5-DiMeO-3,4-MD-Post 489559
(Rhodium: "Synthesis of Myristicinaldehyde/Apiolealdehyde", Novel Discourse)https://www.thevespiary.org/rhodium/Rhodium/chemistry/myristicinaldehyde.shulgin.html
Myristicinaldehyde: 3-MeO-3,4-MD-Post 509800
(Rhodium: "Myristicin Derivatives", Novel Discourse)Post 508799
(Wraith: "Methylenation without KF or PTC", Novel Discourse)Post 504409
(Rhodium: "5-Hydroxypiperonal and Myristicinaldehyde", Novel Discourse)Also:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/5-hydroxy-piperonal.shulgin.html
Post 489659
(Rhodium: "Myristicin & Myristicinaldehyde", Novel Discourse)IR of MyristicinPost 494937
(Islamybad: "Here's the IR spectrum of myristicin from two...", Serious Chemistry)Post 452949
(GC_MS: "myristicinaldehyde", Chemistry Discourse)(
see warning below before attempting this synthesis:)
Warning about TetraNitroMethane and Relatives:Post 355957
(GC_MS: "How dangerous is tetranitromethane?", Chemistry Discourse)3,4-MD-6-OH-Post 464339
(imp: "2-Alkoxy-4,5-methylenedioxybenzaldehyde Synthesis", Novel Discourse)6-OH-2-MeO-3,4-MD-Post 484717
(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
Post 355321
(foxy2: "formylation by the "nitroso" method", Novel Discourse)Post 355336
(Antoncho: "Another EXCELLENT formylation!", Novel Discourse)Post 235460 (missing)
(Antoncho: "Re: Formylations", Chemistry Discourse)Post 422033
(Vitus_Verdegast: "R-T articles that might be interesting", Methods Discourse)https://www.thevespiary.org/rhodium/Rhodium/pdf/bromo2hydroxy-benzaldehydes.pdf
Side Notes:Formylation Mechanism:
Post 481046
(Rhodium: "Magnesium ortho-Formylation Mechanism", Methods Discourse) 
Several Naturally Occuring Aldehydes:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/me3po4.html
