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Citation: WANG Gui-Min, SHAN Yu-Hu, ZHANG Yuan-Yuan, LUO N, WANG You-Yi, JIANG Zhi-Guo, LI Ming-Shi. Acid-Catalyzed Synthesis of Six-Membered Cyclic Acetal from Condensation of Benzaldehyde and Glycerol[J]. Chinese Journal of Applied Chemistry, ;2010, 27(7): 764-768. doi: 10.3724/SP.J.1095.2010.90672 shu

Acid-Catalyzed Synthesis of Six-Membered Cyclic Acetal from Condensation of Benzaldehyde and Glycerol

Key Laboratory of Jiangsu Fine Chemical Engineering, Jiangsu Polytechnic University, Changzhou 213164

Received Date: 16 October 2009
Revised Date: 24 December 2009

Based on the condensation reaction of glycerol with benzaldehyde,the effects of acid catalysts (p-toluenesulfonic acid(PTSA), phosphotungstic acid(PWA), KHSO₄ and FeCl₃,respectively) on the yield of the condensation products and the mass ratio of 5-hydroxyl-2-phenyl-1,3-dioxane(1) to 4-hydroxymethyl-2-phenyl-1,3-dioxolane (2) were investigated. Comparison tests indicated that under the conditions of cyclohexane as water entrainer and n(benzalhydehyde):n(glycerol)=2:3,KHSO₄ gave the best yield (96.8%) of condensation products(compound 1+2) and PTSA yielded the highest proportion (m(1):m(2)=48.6:51.4) of compound 1 in condensation products(compound 1+2). At room temperature, PTSA, PWA, KHSO₄ and FeCl₃ all can,but at -20℃,only PTSA can catalyze the transformation of compound 2 to compound 1. Cis-5-hydroxyl-2-phenyl-1,3-dioxane (1a) was isolated by the catalytic transformation of compound 2 with PTSA at-20℃ and crystallized from a mixture of V(benzene):V(ligroin)=40:60. Compound 1a was obtained by recycling the catalytic transformation of compound 2 in the mother liquor three times in a accumulative yield of 91.1%.
- hydroxylphenyldioxane,
- glycerol,
- benzaldehyde,
- acetals,
- acid-catalyzed condensation
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