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
收藏
页码：1329 / 1331
页数：3
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