Benzyl Bromide → Methyl 4'-(benzyloxy)-[1,1'-biphenyl]-4-carboxylate

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Reaction Steps

4-Benzyloxybenzoic acid chloride and an optically active 1,1,1-trifluoro-2-alkanol were allowed to react to give 1,1,1-trifluoro-2-alkyl 4-benzyloxybenzoate, which was subjected to hydrogenolysis to give 1,1,1-trifluoro-2-alkyl 4-hydroxybenzoate. An alkyl bromide and 2-hydroxynaphthalene-6-carboxylic acid methyl ester 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. The hydrolyzed product was allowed to react with 1,1,1-trifluoro-2-alkyl 4-hydroxybenzoate in the presence of dicyclohexylcarbodiimide to give 6-alkyloxynaphthalene-2-carboxylic acid 4-(1,1,1-trifluoro-2-alkyloxycarbonyl)phenyl ester. ##STR17## (B) 4-Hydroxybiphenyl-4'-carboxylic acid was dissolved in methanol and heated under refluxing in the presence of concentrated sulfuric acid to give 4-hydroxy-biphenyl-4'-carboxylic acid methyl ester. Then the ester and benzyl bromide were dissolved in a solvent such as DMF and the solution was allowed to react in the presence of anhydrous potassium carbonate to give 4-benzyloxybiphenyl-4'-carboxylic acid methyl ester. The compound obtained was subjected to hydrolysis with an aqueous sodium hydroxide solution to give 4-benzyloxy-biphenyl-4'-carboxylic acid. The compound was further allowed to react with thionyl chloride to give 4-benzyloxy-biphenyl-4'-carboxylic acid chloride.

Provenance & Evidence