高等学校化学学报 ›› 1997, Vol. 18 ›› Issue (4): 563.

• 论文 • 上一篇    下一篇

α,β-二甲基脱水丙酮联苯酰的合成

刘宗林, 刘晓崚   

  1. 山东大学化学系, 济南, 250100
  • 收稿日期:1996-04-15 出版日期:1997-05-24 发布日期:1997-05-24
  • 通讯作者: 刘宗林, 男, 55岁, 副教授.
  • 作者简介:刘宗林, 男, 55岁, 副教授.
  • 基金资助:

    中国工程物理研究院科学技术基金

The Synthesis of α,β-Dimethylanhydracetonebenzil

LIU Zong-Lin, LIU Xiao-Ling   

  1. Department of Chemistry, Shandong University, Jinan, 250100
  • Received:1996-04-15 Online:1997-05-24 Published:1997-05-24

摘要: 用两种改进的方法,由联苯甲酰与3-戊酮反应制得α,β-二甲基脱水丙酮联苯酰(Ⅰ).其结构由熔点、IR、1H NMR确定.从1H NMR谱推测:用乙醇作溶剂,加入KOH、联苯甲酰及3-戊酮,于室温搅拌3h后放置3天,所得ⅠA为两对对映体;用苯作溶剂,加入适量聚乙二醇400(PEG400),其它反应物同方法1,加热回流3h,所得产物ⅠA仅为一对对映体.改进的方法都缩短了反应时间.上述两种方法得到的产物,经脱水都为2,5-二甲基-3,4-二苯基环戊二烯酮(Ⅱ).

关键词: &alpha, &beta, -二甲基脱水丙酮联苯酰, 赤系构型, 苏系构型

Abstract: Two improved methods were worked out for the preparation of α,β-dimethylanhy-dracetonebenzil (Ⅰ) by condensation of benzil with 3-pentanone in the presence of KOHasthe catalyst.In method 1, the condensation was carried out with a 3 h stirring in ethanol atroom temperature.After keeping the reaction vessel to stand at room temperature for 3days, the product ⅠAobtained was demonstrated to be a mixture of two pairs of enan-tiomers.But in method 2, the solvent was changed from ethanol to benzene with an additionof suitable amount of polyethyIene glycol PEG-400.After refluxing the mixture for 3 h, theproduct ⅠA'obtained was proved only one pair of enantiomers.When ⅠA and ⅠA'were de-hydrated by heating with Ac2O-H2SO4 separately, both of them formed the same compound3, 4-dipheny1-2, 5-dimethyl cyclopentadienone (Ⅱ).The constituents of ⅠA'ⅠA'and Ⅱwere confirmed mainly by 1H NMRand IR.Finally, it was suggested that ⅠAbe c0nsistedof about equal amount of dl-erythro-Ⅰ and dl-threo-Ⅰ,while ⅠA'is only dl-erythro-Ⅰ.

Key words: α, β-Dimethylahydracetonebenzil, Erythro-Form, Threo-Form

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