2,3,6-Trichlorobenzaldehyde → 1-(2,3,6-Trichlorophenyl)ethanol

Participants

Reaction Steps

General Procedure CC: To a solution of 2,3,6-trichlorobenzaldehyde (1.00 g, 4.77 mmol) in THF (10 mL) was added MeMgBr/butyl ether (1M, 5.72 mL, 5.72 mmol) at 0° C. under nitrogen, the resulting mixture was allowed to warm to rt and stirred overnight. The mixture was quenched with sat. aq. NH4Cl (15 mL) at 0° C., then diluted with Et2O (15 mL), the organic phase was washed with brine (20 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to give the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.69 (d, J=6.8 Hz, 3H), 2.97 (br. s., 1H), 5.67 (q, J=6.8 Hz, 1H), 7.30 (d, J=3.0 Hz, 1H), 7.35-7.38 (m, 1H).

Provenance & Evidence