Methanol → Methyl 3-hydroxypivalate

Participants

Reaction Steps

3-Hydroxy-2,2-dimethylpropanoic acid (15.00 g, 127.0 mmol) was dissolved in a solution of MeOH (200 mL) and conc. H2SO4 (13.5 g, 254 mmol) and stirred at reflux for 16 h. The reaction mixture was concentrated in vacuo, diluted with EtOAc (100 mL), washed with water (2×50 mL), sat. NaHCO3 (aq) (50 mL), water (50 mL), brine (1×50 mL), and dried (Na2SO4). Organic solvent was removed in vacuo to afford methyl 3-hydroxy-2,2-dimethylpropanoate (6.4 g, 57.2%) as a colorless liquid. 1H NMR (400 MHz, DMSO-d6): δ 3.71 (s, 3H), 3.56 (s, 2H), 2.05-2.04 (m, 1H), 1.19 (s, 6H).

Provenance & Evidence