Sodium Chloride → 3-(3-Hydroxyprop-1-en-1-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

1.73 g of (E)-3-(3-cyanophenyl)acrylic acid was suspended in 8.7 ml of tetrahydrofuran. To the suspension was added 1.11 g of triethylamine. To the mixture was dropwise added a solution of 1.14 g of ethyl chlorocarbonate dissolved in 3.0 ml of tetrahydrofuran, at -20° to -10° C. The mixture was stirred for 30 minutes at 0° C. The reaction mixture was mixed with 2 ml of ethyl acetate and 20 ml of a saturated aqueous sodium chloride solution. The organic layer was separated and washed with a saturated aqueous sodium chloride solution to obtain a solution containing a mixed acid anhydride of (E)-3-(3-cyanophenyl)acrylic acid. To this solution was added 380 mg of sodium borohydride with ice-cooling. The mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 20 ml of water and 10 ml of ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/acetone=5/1) to obtain 1.37 g of colorless oily (E)-3-(3-cyanophenyl)allyl alcohol.

Provenance & Evidence