Benzyl alcohol, p-nitro-, benzoate → Benzoic Acid

Participants

Reaction Steps

To a solution of 160 mg of p-nitrobenzyl benzoate in 5 ml of tetrahydrofuran and 5 ml of 0.35M phosphate buffer (pH 6.1) was added 1.6 g of zinc powder and the mixture was stirred for 3 hours at room temperature. After the reaction, the reaction mixture was filtered using Celite, and the pH of the filtrate was adjusted to an alkaline side by adding sodium carbonate. It was then washed with 10 ml of ethyl acetate twice. The aqueous layer was acidified and then extracted with ethyl acetate (10 ml×3). The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by chromatography to give 58 mg (76.4%) of benzoic acid. m.p. 121°-122° C.

Provenance & Evidence