Acetone → (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate

Participants

Reaction Conditions

Reaction Steps

(E)-Methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (15 g) was dissolved in acetone (200 ml) and the solution was cooled to 2° C. A solution of silver nitrate (22.35 g) in water (200 ml) at 4° C. was added to this. The temperature rose 12° C. After stirring for 40 minutes the green/grey precipitate which had formed was filtered off and the filtrate partitioned between water and diethyl ether. The diethyl ether layer was washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to give an oil which was purified by chromatography on silica gel, eluting with diethyl ether, to give (E)-methyl 2-[2-(hydroxymethyl)phenyl]-3-methoxypropenoate as a viscous oil (6.33 g, 54%). 1H NMR (CDCl3): 2.3(t, 1H), 3.7(s, 3H), 3.8(s, 3H), 4.5(d, 2H), 7.1(m, 1H), 7.2-7.4(m 2H), 7.5(m, 1H), 7.6(s, 1H) ppm.

Provenance & Evidence