3,4,5-Trimethoxybenzaldehyde Explained
3,4,5-Trimethoxybenzaldehyde is an organic compound and a biochemical. Within this class of compounds, the chemical is categorized as a trisubstituted aromatic aldehyde.
Uses
3,4,5-Trimethoxybenzaldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including trimethoprim,[1] [2] cintriamide, roletamide, trimethoquinol (aka tretoquinol), and trimazosin as well as some psychedelic phenethylamines.[3] [4] [5]
Preparation
Industrial scale
For industrial applications the chemical is synthesized from p-cresol using aromatic substitution with bromine followed by nucleophilic substitution with sodium methoxide. Oxidation of the methyl group to an aldehyde can occur via various synthetic methods.
Laboratory scale
At the laboratory scale the chemical is conveniently synthesized from vanillin[6] or from Eudesmic acid's Acyl chloride via Rosenmund reduction.[7]
Notes and References
- Book: Asim Kumar Mukhopadhyay. Industrial Chemical Cresols and Downstream Derivatives. 2004. CRC Press. New York. 9780203997413. 81. 2 June 2014.
- Stenbuck, P.; Hood, H. M.; 1962,
- Kindler, Karl. Peschke, Wilhelm. amp. Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen VI. Über Synthesen des Meskalins. Archiv der Pharmazie. 1932. 270. 7. 410–413. 10.1002/ardp.19322700709. 93188741.
- Benington, Fred. Morin, Richard. amp. An Improved Synthesis of Mescaline. Journal of the American Chemical Society. 1951. 73. 3. 1353. 10.1021/ja01147a505.
- Book: Shulgin, Alexander. Shulgin, Ann. amp. PiHKAL: A Chemical Love Story. 1991. Transform Press. Lafayette, CA. 9780963009609.
- Manchanda Percy . Belicaa, Peter . Wonga, Harry . amp. Synthesis of 3,4,5-Trimethoxybenzaldehyde. Synthetic Communications. 1990. 20. 17. 2659–2666. 10.1080/00397919008051474.
- Rachlin, A.. Gurien, H.. Wagner, D.. amp. Aldehydes from Acid Chlorides by modified Rosenmund Reduction: 3,4,5-Trimethoxybenzaldehyde. Organic Syntheses. 1971. 51. 8. 10.15227/orgsyn.051.0008.
