Sodium Hydroxide → 2-Iodophenylacetic acid

Participants

Reaction Steps

A solution of 2-(2-iodophenyl)acetonitrile (2.82 g) in a mixture of 1:1 (v/v) ethanol/water (70 ml) was treated with sodium hydroxide (2.4 g) and stirred at reflux for 4 hours. The resultant solution was cooled to ambient temperature, concentrated to 30 ml, diluted with water (100 ml) and washed with ethyl acetate (2×100 ml). The organic layers were combined and extracted with 2M aqueous sodium hydroxide solution (100 ml). The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and filtered. The solid collected was washed with water and vacuum dried to give 2-(2-iodophenyl)acetic acid (1.45 g) as a solid, m.p. 110-113° C.; microanalysis; found: C, 36.9; H; 2.7%; C8H7IO2 requires: C, 36.7; H, 2.7%; NMR: 3.7(2H, s), 7.0(1H, m), 7.4(2H, m), 7.8(2H, d); 12.5(1H, br s).

Provenance & Evidence