Sodium Hydroxide → 7-Cyanonaphthalene-2-carboxylic acid

Participants

Reaction Steps

A solution of NaOH (1.36 g, 34 mmol) in water (35 mL) was added dropwise to a solution of 191 (4.95 g, 24 mmol) in EtOH (100 mL) and CH2Cl2 (30 mL) and the mixture was stirred for 15 h. Water was added to dissolve the white solid and the mixture was extracted with CH2Cl2 (×2) and EtOAc. The aqueous portion was acidified (pH 2) with aqueous HCl (2N) and the resulting precipitate was filtered off, washed with water, and dried in a vacuum desiccator to give 7-cyano-2-naphthoic acid (192) (4.60 g, 99%), as a colorless powder: mp 279-283° C.; lit. mp [Aust. J. Chem., 1965, 18, 1351] 286-288° C.; 1H NMR [(CD3)2SO] δ 13.25 (br s, 1H), 8.81 (s, 1H), 8.75 (s, 1H), 8.20 (d, J=8.5 Hz, 1H), 8.17 (d, J=8.5 Hz, 2H), 8.15 (d, J=8.5 Hz, 2H), 7.92 (dd, J=8.5, 1.3 Hz, 1H).

Provenance & Evidence