Ethanol → 2-(4-Methoxyphenyl)cyclopropane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a 100 mL RB flask fitted with magnetic stirrer was charged with 20 mL of tetrahydrofuran. To the stirred solvent was added ethyl 2-(4-methoxyphenyl)cyclopropanecarboxylate (8 g, 36 mmol). The reaction mixture was cooled to 0° C. and sodium hydroxide (2.1 g, 54 mmol) in water (5 mL) was added drop wise, followed by ethanol (10 mL). The reaction mixture was stirred for 8 h at room temperature. The reaction mixture was concentrated to distill off the solvent; the crude was acidified with 1N hydrochloric acid to make acidic pH and extracted with ethyl acetate (50 mL). The layers were separated; the organic layer was washed with brine solution (20 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as off white solid (6.5 g, yield: 94.2%). 1H NMR (300 MHz, CDCl3): δ 6.96-6.99 (d, 2H), 6.74-6.77 (d, 2H), 3.71 (s, 3H), 2.46-2.53 (m, 1H), 1.72-1.78 (m, 1H), 1.52-1.58 (m, 1H), 1.27-1.32 (m, 1H).

Provenance & Evidence