Anise oil as para-methoxyamphetamine (PMA) precursor (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/anethole.pma.precursor.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/anethole.pma.precursor.pdf), anethole doesn't have to bee isolated from anise oil which is exactly what SWIM is gonna do. The only problem is whether he should use the bichromate method from above (ca 50%, looks straightforward but K2Cr2O7 is toxic/suspicious) or the great-looking permanganate on alumina method (like here:Post 237918 (missing)
(jim: "Simple KMnO4 method of benzaldehyde formation", Chemistry Discourse)Post 293705 (https://www.thevespiary.org/talk/index.php?topic=6380.msg29370500#msg29370500)
(otto: "using permanganate", Chemistry Discourse)Post 511939 (https://www.thevespiary.org/talk/index.php?topic=11133.msg51193900#msg51193900)
(Kinetic: "Cinnamic acid to benzaldehyde", Newbee Forum)). The KMnO4 procedure would bee ridiculously cheap, excellent yielding (ca 95%), and easy to work up. The obvious problem is gargantuic amounts of solvent and oxidizer. SWIM has an impression this could be reduced substantially, good stirring warranted, as anethole is easily soluble in DCM and wonders whether someone here has tried this. If not, he is going to experiment on this himself with like 3-5x less solvent/oxidizer and hope it works.Post 508451 (missing)
(azole: "ethylenediamine as a catalyst", Methods Discourse), yield 97%).Post 245040 (https://www.thevespiary.org/talk/index.php?topic=11784.msg24504000#msg24504000)
(Rhodium: "O Leminger's Phenethylamines - posted by Karel", Novel Discourse)) but was unable to find any published specifics on p-MeO-nitrostyrene Anyone? If this fails, he is gonna try Urushibara type catalyst likehttps://www.thevespiary.org/rhodium/Rhodium/chemistry/amph.urushibara.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/amph.urushibara.html)
. If this fails, in a fit of despair he will try to use the well-known Al/Hg method and/or Clemmensen conditions 9(Post 507331 (https://www.thevespiary.org/talk/index.php?topic=9013.msg50733100#msg50733100)
(Rhodium: "Clemmensen reduction of nitrostyrenes", Methods Discourse)). Again, no specifics were found on p-methoxynitrostyrene. Would bee glad to hear your comments on that.Post 488372 (https://www.thevespiary.org/talk/index.php?topic=7492.msg48837200#msg48837200)
(Rhodium: "Aromatic Iodination with I2 and Urea-H2O2 (UHP)", Chemistry Discourse)) looks promising, then we have oxone/KI (Post 428701 (https://www.thevespiary.org/talk/index.php?topic=11604.msg42870100#msg42870100)
(Barium: "Can it be true?", Novel Discourse) andhttps://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.aromatic.iodination.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.aromatic.iodination.html)
, BTW is the formation of 2C-I under these conditions confirmed?), oxone/KBr (https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.aromatic.bromination.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/oxone.aromatic.bromination.html)
), iodine/KNO3, plain old Br2/AcOH, HBr/H2O2, iodine/silver sulfate etc... Hell, KI/persulfate should work also... SWIM is gonna try the above methods more or less in the order listed. Any advices?Post 173322 (https://www.thevespiary.org/talk/index.php?topic=12031.msg17332200#msg17332200)
(uemura: "TMA2-P2NP: an alternative approach", Novel Discourse)Post 348662 (https://www.thevespiary.org/talk/index.php?topic=9782.msg34866200#msg34866200)
(Antibody2: "2,3-dimethoxy-4,5-methylenedioxyphenylethylamine", Methods Discourse)