3,4,5-Trimethoxybenzoic Acid → N,3,4,5-tetramethoxy-N-methyl-Benzamide

Participants

Reaction Steps

3,4,5-Trimethoxybenzoic acid was allowed to react with oxalyl chloride, and the resulting acid chloride was allowed to react with N,O-dimethylhydroxyamine hydrochloride to obtain N,3,4,5-tetramethoxy-N-methylbenzamide. The resulting compound was allowed to react with 4-phenylbutylmagnesium chloride to obtain 5-phenyl-1-(3,4,5-trimethoxyphenyl)pentan-1-one. The resulting compound was allowed to react with lithium diisopropylamine and methyl2-[4-(bromomethyl)phenoxy]benzoate in the presence of N,N,N′,N″,N″-pentamethyldiethylenetriamine to obtain methyl2-{4-[5-phenyl-2-(3,4,5-trimethoxybenzoyl)pentyl]phenoxy}benzoate. The resulting compound was hydrolyzed with sodium hydroxide to give the title compound having the following physical properties.

Provenance & Evidence