p-Nitrobenzyl benzoate → Benzoic Acid

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.

1. customAfter the reaction
2. filtrationthe reaction mixture was filtered
3. additionby adding sodium carbonate
4. washIt was then washed with 10 ml of ethyl acetate twice
5. extractionextracted with ethyl acetate (10 ml×3)
6. washThe organic layer was washed with water
7. dry with materialdried over magnesium sulfate
8. customThe solvent was removed under reduced pressure
9. customthe residue was purified by chromatography

ORD record

ord-ee32cde2b9ce469f944664c8e3e466b0

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04977256