Selective demethylation of 3,4-dimethoxybenzaldehyde
✍ Scribed by R.H. Prager; Y.T. Tan
- Book ID
- 104241034
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- French
- Weight
- 161 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A recent report by Brossi (1) on the seleotive acid-catalpaed demethylation of the methoxyl group substituted m to a carbonyl function prompts this report of similar work.
We were interested in developing a method for the seleotive, stepwise demethylation of the aoridoae alkaloid melioopiciae, (I), and chose to use veratraldme as a model compound to et-the effeot of varying the demethylating agent, solvent, and tmpclwturs.
The use of Lewis aaids, such as aluminiue chloride, boron triohloride, boron tribromide and pyridinium hydrochloride was first studied. In agreement with the work of
📜 SIMILAR VOLUMES
Single-crystal X-ray study T = 293 K Mean '(C±C) = 0.003 A Ê R factor = 0.045 wR factor = 0.115 Data-to-parameter ratio = 12.2 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Demethylation of asymmetically substituted 2,6-dimethoxybenzaldehydes with magnesium iodide etherate regioselectively single 6-methoxysalicylaidehydes derived from the more unstable chelation.
In the title compound, C~15~H~15~N~3~O~4~·H~2~O, the organic molecule exists in the keto–imine tautomeric form. The benzene ring makes a dihedral angle of 49.9 (2)° with the pyridine ring. The molecules pack in a three-dimensional framework structure by a combination of O—H...O, O—H...N, N—H...O and