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水溶剂中芳醛与5,5-二甲基-1,3-环己二酮的反应
引用本文:史达清,庄启亚,陈景,王香善,屠树江,胡宏纹. 水溶剂中芳醛与5,5-二甲基-1,3-环己二酮的反应[J]. 有机化学, 2003, 23(7): 694-696
作者姓名:史达清  庄启亚  陈景  王香善  屠树江  胡宏纹
作者单位:1. 徐州师范大学化学系,徐州,221009;南京大学化学系,南京,210093
2. 徐州师范大学化学系,徐州,221009
3. 南京大学化学系,南京,210093
基金项目:江苏省青蓝工程(No.QL9801)资助项目
摘    要:芳醛1与5,5-二甲基-1,3-环己二酮(2)在氯化三乙基苄基铵(TEBA)催 化下在水中生成2,2'-芳业甲基双(3-羟基-5,5-二甲基-2-环己烯-1-酮 )(3),若在体系中有对甲苯磺酸存在时则生成3,3,6,6-四甲基-9-芳基- 1,8-二氧代八氢化氧杂蒽(4)或3,3-二甲基-9-(3-羟基-5,5-二甲基 -2-环己烯-1-酮-2-基)-1-氧代四氢代氧杂蒽(6)而不是生成3,产率接 近定量。

关 键 词:芳香族醛  环己二酮  氯化三乙基苄基铵  氧杂蒽 P    苯磺酸 P
修稿时间:2002-08-13

Reaction of Aromation Aldehydes with 5,5-Diemthyl-1,3- cyclohexandione in Water
SHI,Da-Qing ZHUANG,Qi-Ya CHEN,Jing WANG,Xiang-Shan,TU,Shu-Jiang HU,Hong-Wen. Reaction of Aromation Aldehydes with 5,5-Diemthyl-1,3- cyclohexandione in Water[J]. Chinese Journal of Organic Chemistry, 2003, 23(7): 694-696
Authors:SHI  Da-Qing ZHUANG  Qi-Ya CHEN  Jing WANG  Xiang-Shan  TU  Shu-Jiang HU  Hong-Wen
Affiliation:Department of Chemistry, Xuzhou Normal University;Department of Chemistry, Nanjing University
Abstract:The environmental friendly reaction of aromatic aldehydes with 5,5-dimethyl-1,3-cyclohexandione giving 2,2'-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) (3) was carried out in water in the presence of trienthylbenzylammonium chloride (TEBA). While TsOH existed in the reaction, 3,3,6,6-tetramethyl-9-aryl-1,8-dioxooctahydroxanthene (4) or 3,3-dimethyl-9-(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one-2-yl)-1-oxotetrahydro-xanthene (6) rather than 3 was obtained with excellent yield.
Keywords:aromatic aldehyde   5  5-dimethyl-1  3-cyclohexandione   water   environment-friendly reaction
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