Acetaldehyde → 1-(2-Fluoro-6-methoxyphenyl)ethanol

Participants

Reaction Steps

n-Butyl lithium (3.9 mls of 1.14M in hexane) was added dropwise to a solution of 3-fluoroanisole (0.45 mls) in dry tetrahydrofuran (10 mls) at -75° under nitrogen. The solution was kept at -75° for 1 hour, and then acetaldehyde (0.68 mls) was added dropwise and the mixture allowed to warm up. 2M Hydrochloric acid (20 mls) was added, the mixture was extracted with ether, the organic solution was dried (MgSO4) and the solvent was evaporated. The product was distilled to give the title compound as an oil (0.4 g). NMR (CDCl3) δ 7.17 (1H, d of t, 4-H), 6.75-6.6(2H, m, 3-H, 5-H), 5.24(1H, m, CHO--), 3.89(3H, s, OCH3), 3.27 (1H, d OH), 1.56(3H, d, CH3).

Provenance & Evidence