Hydrochloric Acid → 3-(4-Methoxyphenyl)-2,2-dimethylpropanoic acid

Participants

Reaction Steps

Potassium tert-butoxide (38.0 g, 0.34 mol) was added to a solution of ethyl 2,2-dimethyl-3-(4-methoxyphenyl)propanoate (40.0 g, 0.17 mol) in a mixture of water (4 mL) and tetrahydrofuran (800 mL) at room temperature and stirred for 16 h. The pH of the reaction mixture was adjusted to ˜2 with 2 N HCl (250 mL) and extracted with EtOAc (800 mL). Aqueous layer was saturated with NaCl and extracted again with EtOAc (800 mL). The combined organic layers were washed with brine (350 mL), dried over Na2SO4, and concentrated to afford 34.0 g (96%) of 2,2-dimethyl-3-(4-methoxyphenyl)propanoic acid as a gummy oil; 1H NMR (200 MHz, CDCl3) δ 7.08 (d, J=8.4 Hz, 2H), 6.80 (d, J=8.4 Hz, 2H), 3.78 (s, 3H), 2.83 (s, 2H), 1.19 (s, 6H).

Provenance & Evidence