Hydrochloric Acid → (2E)-3-(2-Chlorophenyl)-2-propen-1-ol

Participants

Reaction Steps

A solution of 2-chlorocinnamic acid (5.00 g, 27.4 mmol) in THF (50 mL) was slowly added to a suspension of NaBH4 (1.24 g, 32.9 mmol) in THF (50 mL) at room temperature. The mixture was stirred until evolution of gas ceased. A solution of 12 (3.47 g, 13.7 mmol) in THF (50 mL) was then added and the mixture was stirred at room temperature for 1 h. Aqueous 3 N HCl solution (10 mL) was added carefully and the mixture was extracted with Et2O. The combined organic layers were successively washed with aqueous 1 N NaOH solution and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2:(CH3)2CO, 95:5) to yield the title compound (2.86 g, 62% yield).

Provenance & Evidence