Reduction of carboxylic acids into alcohols using NaBH4 in the presence of catechol and/or CF3COOH

Suseela, Yantrapragada ; Periasamy, Mariappan (1992) Reduction of carboxylic acids into alcohols using NaBH4 in the presence of catechol and/or CF3COOH Tetrahedron, 48 (2). pp. 371-376. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)88148-5

Abstract

Reaction of aliphatic carboxylic acids (1 eq) using NaBH4 (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 NaBH4 (2 eq), catechol (2 eq) and CF3COOH (1 eq) gives the aliphatic alcohols in 87–94% yields. Reductions using aliphatic acids (1 eq), NaBH4 (1 eq) and CF3COOH (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).

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