Hydrochloric Acid → Methyl (2-hydroxyphenyl)acetate

Participants

Reaction Steps

2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)]. The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours). The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased. The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92% yield) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1 ; 1H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H, s), 6.80-6.95 (2H, m), 7.05-7.10 (1H, m), 7.15-7.25 (1H, m), 7.40 (1H, s) ppm.

Provenance & Evidence