Methanol → 2-(3-Methoxyphenyl)-2-methylpropanoic acid

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask, potassium hydroxide (35.4 g, 631 mmol) and water (225 mL, 12500 mmol) was added at 100° C. 2-(3-methoxy-phenyl)-2-methyl-propionitrile (44.20 g, 252.2 mmol) in Methanol (25.0 mL, 617 mmol) was added to the reaction mixture. The reaction was then heated to reflux at 130° C. over night. TLC suggested starting material. Potassium hydroxide (35.4 g, 631 mmoles) in water (50 mL) was added. The reaction was heated for 5 days. The reaction was partitioned with water (700 mL). The aqueous was acidified with concentrated HCl to pH 1. The solid was filtered and washed with water and EtOAc. The organic layer was separated. The aqueous was extracted with EtOAc (3×400 mL). The combined organic was washed with brine, and dried over MgSO4. The solid was then filtered and washed with EtOAc. The solvent was removed under vacuum to afford a brown oil. The oil was triturated with hexane to afford 2-(3-methoxy-phenyl)-2-methyl-propionic acid as a light yellow solid (36.2 g. 74%). 1H-NMR (DMSO-D6, 400 MHz): δ 12.30 (s, 1H), 7.24 (t, 1H), 6.90 (d, 1H), 6.75-6.88 (m, 2H), 3.74 (s, 3H), 1.45 (s, 6H)

Provenance & Evidence