Zhang Junsong
2012
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China Surfactant Detergent & Cosmetics
Abstract
With benzoyl peroxide and boric acid as catalyst,3-methyl-4-oxooctanoic acid was synthesized by free radical addition reaction of valeraldehyde and crotonic acid as starting materials.Then it was reduced by sodium borohydride,and whisky lactone with cis and trans isomeric structure was obtained by intramolecular dehydration under the action of dilute sulfuric acid.The cis-trans isomers were separated by column chromatography,with eluent composed of V(petroleum ether)∶ V(ethyl acetate)=5∶ 1.Structure of the two targeted products were confirmed by IR,1HNMR and MS.Effect of factors on the yield such as kind of solvent,solvent amount,reaction time,dosage of sodium borohydride and dilute sulfuric acid were investigated.Optimum conditions for the reaction were found as follows:ethanol as solvent,m(ethanol)∶ m(3-methyl-4-oxooctanoic acid)=3∶ 1,reaction time 2 h at room temperature,m(sodium borohydride)∶ m(3-methyl-4-oxooctanoic acid)=1∶ 4;m(12% sulfuric acid)∶ m(3-methyl-4-oxooctanoic acid)=10∶ 1.Overall yield of the complete synthesis process achieves 61.9%.