2-HYDROXY-5-METHOXYBENZONITRILE

673-22-3

39835-11-5

The general procedure for the synthesis of 2-hydroxy-4-methoxybenzonitrile from 2-hydroxy-4-methoxybenzaldehyde is as follows: 2-hydroxy-4-methoxybenzaldehyde (20 g, 128.8 mmol), sodium acetate (35.05 g, 257.6 mmol), and nitroethane (19 mL, 257.6 mmol) were dissolved in glacial acetic acid (100 mL) and the mixture was heated under mild reflux conditions for 12 hours. Upon completion of the reaction, the reaction mixture was slowly poured into about 1000 mL of ice water (1:1 ratio of ice to water). The product was extracted with ethyl acetate (3 x 200 mL). The organic phases were combined and washed with sodium bicarbonate solution until the pH of the aqueous layer was about 8. Subsequently, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum to afford 2-hydroxy-4-methoxybenzonitrile as a yellow oil (16.5 g, 86% yield).