Methanol → Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

Participants

Reaction Steps

An alkyl bromide and 2-hydroxy-6-methylcarbonyloxynaphthalene were allowed to react in the presence of potassium carbonate in a solvent such as dimethylformamide and then subjected to hydrolysis with an aqueous sodium hydroxide solution. The hydrolyzed product was allowed to react with the aforementioned 4'-(1,1,1-trifluoro-2-alkyloxycarbonyl) biphenyl-4-carboxylic acid chloride to give 6-alkyloxynaphthalene 4-(1,1,1-trifluoro-2-alkyloxycarbonyl)-biphenyl-4'-carboxylate. ##STR19## (D) 4-Hydroxybiphenyl-4'-carboxylic acid was dissolved in methanol and heated under refluxing in the presence of concentrated sulfuric acid to give 4-hydroxybiphenyl-4'-carboxylic acid methyl ester. Then the ester and benzyl chloride were dissolved in a solvent such as DMF and allowed to react in the presence of anhydrous potassium carbonate to give 4-benzyloxybiphenyl-4'-carboxylic acid. The carboxylic acid was further allowed to react with thionyl chloride to give 4-benzyloxybiphenyl-4'-carboxylic acid chloride.

Provenance & Evidence