Chem. J. Chinese Universities ›› 1997, Vol. 18 ›› Issue (4): 563.

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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

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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