Sodium borohydride → 2-Cyano 3-(2,6-dichlorophenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (1121 mmol, 42.4 g) was added, in portions over a period of 45 minutes, to a stirred suspension of 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (448 mmol, 108.5 g) in MeOH (1 L) and aqueous saturated sodium bicarbonate (500 mL) at 0° C. After stirring at 0° C. for 30 minutes the cooling bath was removed and the reaction was allowed to warm to room temperature. Stirring was continued at room temperature for 3 hours and the reaction mixture was then left to stand overnight. The reaction mixture was partially concentrated under reduced pressure and the remaining aqueous was diluted with water and then acidified with 5 N HCl. Extraction with ether followed by drying over sodium sulfate, filtering and concentrating under reduced pressure afforded 110 g of 2-cyano-3-(2,6-dichlorophenyl)propanoic acid (100% yield).

Provenance & Evidence