Reduction of Aromatic Aldehydes, Ketones with Acyloxy Substituent at the Ortho-position by NaBH4 in the Presence of Waters

Chemical Research in Chinese Universities ›› 1999, Vol. 15 ›› Issue (2): 182-187.

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Reduction of Aromatic Aldehydes, Ketones with Acyloxy Substituent at the Ortho-position by NaBH₄ in the Presence of Waters

WAN Xin-hua, ZHOU Hong-bing, XIE Ren, ZHANG Dong, FENG Xin-de, ZHOU Qi-Feng

Department of Polymer Science & Engineering, Peking University, Beijing, 100871

Received:1998-06-05 Online:1999-04-24 Published:2011-08-17
Supported by:
Supported by the National Natural Science Foundation of China(No.59873001).

Abstract

Abstract: n unusual reduction of some aromatic aldehydes, ketones by sodium borohydride was discovered. In a THF/H₂O or DMSO/H₂O solvent system the aromatic aldehydes, ketones with acyloxy substituent on the ortho-position to the carbonyl group can be reduced to the corresponding alkyl phenols. This unusual reduction is applicable also to the corresponding alcohols of all the above aldehydes, ketones. A putative mechanism was suggested. In addition to the above aldehydes, ketones, benzyl alcohols, certain 4-acyloxybenzyl esters(probably also the 2-substituted analogues) such as 4-benzoyloxybenzyl benzoate was also found to be reduced to methylphenol by this unusual reduction.

Key words: Reduction, Sodium borohydride, Benzaldehyde, Aromatic ketone

WAN Xin-hua, ZHOU Hong-bing, XIE Ren, ZHANG Dong, FENG Xin-de, ZHOU Qi-Feng . Reduction of Aromatic Aldehydes, Ketones with Acyloxy Substituent at the Ortho-position by NaBH₄ in the Presence of Waters[J]. Chemical Research in Chinese Universities, 1999, 15(2): 182-187.

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Reduction of Aromatic Aldehydes, Ketones with Acyloxy Substituent at the Ortho-position by NaBH₄ in the Presence of Waters

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