Methanol → Methyl 3-hydroxypivalate

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).

1. temperatureat reflux for 16 h
2. concentrationThe reaction mixture was concentrated in vacuo
3. additiondiluted with EtOAc (100 mL)
4. washwashed with water (2×50 mL), sat. NaHCO3 (aq) (50 mL), water (50 mL), brine (1×50 mL)
5. dry with materialdried (Na2SO4)
6. customOrganic solvent was removed in vacuo

ORD record

ord-0a6700a2f3b447f1beb84a601f514a4a

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193719B2