Reduction of carboxylic acids into alcohols using NaBH 4 in the presence of catechol and/or CF 3COOH

Abstract

Reaction of aliphatic carboxylic acids (1 eq) using NaBH 4 (2 eq) and catechol (2 eq) in THF at 25°C gives the corresponding alcohols in 47–49% yield besides the unreacted carboxylic acids. Reduction of aliphatic carboxylic acids (1 eq) using NaBH 4 (2 eq), catechol (2 eq) and CF 3COOH (1 eq) gives the aliphatic alcohols in 87–94% yields. Reductions using aliphatic acids (1 eq), NaBH 4 (1 eq) and CF 3COOH (1 eq) also give aliphatic alcohols in 93–95% yields. Under these conditions, the aromatic acids give poor yields. However, capric acid (1 eq) is selectively reduced to 1-decanol in 72% yield in the presence of benzoic acid (1 eq).