Tetrahedron

Reductive esterification of aromatic aldehydes using Zn/Ac 2 O/imidazole or Zn/Yb (OTf) 3/(RCO) 2 O system

T Hirao, S Santhitikul, H Takeuchi, A Ogawa, H Sakurai

Index: Hirao, Toshikazu; Santhitikul, Sirida; Takeuchi, Hiroki; Ogawa, Akiya; Sakurai, Hidehiro Tetrahedron, 2003 , vol. 59, # 51 p. 10147 - 10152

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Citation Number: 8

Abstract

Benzaldehydes are reduced by metallic zinc in the presence of Ac2O and imidazole, giving the corresponding benzyl acetates in good yields. Reductive esterification of aromatic aldehydes is also carried out via gem-diacetoxy compounds. Carbonyl compounds are readily converted to the gem-diacyloxy compounds in excellent yields on treatment with 2molar amounts of acid anhydride and 10mol% of Yb (OTf) 3 in MeCN at room ...

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