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ChemicalBook CAS DataBase List ALLYL BENZOATE

ALLYL BENZOATE synthesis

15synthesis methods
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Yield: 85%

Reaction Conditions:

Stage #1:benzoic acid with copper;sodium iodide in water under 760.051 Torr; for 1 h;Green chemistry;
Stage #2:3-chloroprop-1-ene in water under 760.051 Torr; for 5 h;Reflux;Green chemistry;

Steps:

General procedure for preparation of unsaturated esters
General procedure: A mixture of 0.1mol carboxylate(mass=0.1M), 2.0g TC-1~6, 0.75g NaI, 0.05g Cu and 20mL H2O was put into a flask equipped with stirring device, reflux condenser, thermometer and dropping funnel. The mixture was heated up to 35~40 for 1h. Then quantitative allyl chloride according to n(Cl): n(COONa)=2:1 was added dropwise during 2h. After refluxing for 2~4h, the excess of allyl chloride was distilled off. The reaction mixture was cooled to room temperature and filtered out quaternary ammonium salts and Cu powder. Then, organic layer was separated, washed with water, and dried overnight with MgSO4. The crude product was purified by vacuum distillation in presence of high boiling point solvent or by a silica-gel column chlomatography with petroleum ether and EtOAc. Products were obtained in excellent yield.

References:

Liang, Zheng Yong;Wang, Li Li;Liu, Hui;Huang, Jin Shuo [Journal of the Chilean Chemical Society,2013,vol. 58,# 1,p. 1558 - 1561]

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