Hydroxyphenylacetic acid → Benzeneacetic acid, 4-hydroxy-, methyl ester

Participants

Reaction Steps

4-Hydroxyphenylacetic acid (1.75 g) was dissolved in methanol (30 ml) and 10M aqueous hydrochloric acid (0.15 ml) was added and heated to reflux for 15 hours. After cooling to room temperature, triethylamine (1 ml) was added, the mixture concentrated, purified by flash chromatography using silica gel (30 g) and eluted with ethyl acetate-hexane (2:8 volume by volume) to give Methyl 4-Hydroxyphenylacetate (4) (1.693 g). This was confirmed by spectroscopy--1H NMR (CDCl3) δ 3.58 (s, 2 H), 3.73 (s, 3 H), 6.75 (d, 2 H), 7.10 (d, 2 H).

Provenance & Evidence