2,2-Dimethoxypropane → Methyl 4-bromo-alpha-hydroxybenzeneacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-bromophenyl)-2-hydroxyacetic acid (5.00 g, 21.6 mmol) in MeOH (10 mL) was added 2,2-dimethoxypropane (3.39 g, 32.6 mmol) and 4-methylbenzene-1-sulfonic acid (2.00 mg, 0.0100 mmol). The resulting solution was stirred at 55° C. overnight. The reaction mixture was concentrated under reduced pressure, and H2O (100 mL) was added. The resulting solids were collected by filtration and washed with hexane to obtain compound 9a as a gray solid (4.00 g, 72% yield). 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.54-7.51 (m, 2H), 7.35-7.28 (m, 2H), 5.18-5.16 (m, 1H), 3.793 (s, 3H), 3.51-3.49 (m, 1H).

Provenance & Evidence