Selective reduction of 2-[(benzoyl)oxy]benzaldehydes without intramolecular transesterification

被引：4

作者：

Pugh, C ^{[1
]}

机构：

[1] Univ Akron, Maurice Morton Inst Polymer Sci, Akron, OH 44325 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005799y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NaBH4 reduction of 2,5-bis[(4'-(n-alkoxy)benzoyl)oxy]benzaldehydes produces primarily the rearranged phenol, which does not generate liquid crystalline phases when laterally attached to a polymer backbone. Rearrangement is prevented by quenching the intermediate benzyl alkoxide with a weak acid. For example, 2,5-bis[(4'-(methoxy)benzoyl)oxy]benzaldehyde is selectively reduced to 2,5-bis[(4'-(methoxy)benzoyl)oxy]benzyl alcohol with less than 5% intramolecular transesterification using 2-3 equiv of NaBH4 in the presence of 20-30 equiv of acetic acid (1:10 NaBH4/AcOH).

引用

页码：1329 / 1331

页数：3

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