Homovanillic Acid → 4-(Acetyloxy)-3-methoxybenzeneacetic acid

Participants

Reaction Steps

A mixture of (4-hydroxy-3-methoxyphenyl)acetic acid (380 mg, 2.088 mmol) and H3PO4 (2 drops) in about 20 mL of Hac/Ac2O (v/v=1:1) was refluxed overnight, and then concentrated to dryness in vacuo. The residue was diluted with water (50 mL), and the result mixture was extracted with ethyl acetate (2*50 mL). The combined organic phase was washed with brine (100 mL) and dried over Na2SO4 and concentrated to give [4-(acetyloxy)-3-methoxyphenyl]acetic acid. 1H-NMR (400 MHz, CDCl3) δ ppm 6.97 (d, J=7.8 Hz, 1H), 6.84˜6.89 (m, 2H), 3.81 (s, 3H), 3.61 (s, 2H), 2.29 (s, 3H).

Provenance & Evidence