Syntheses of Arenediacetic Esters and Acetonyl-Substituted Arylacetic Esters by Means of Friedel-Crafts Reaction with α-Acyl-α-chlorosulfides

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Friedel-Crafts reaction of the phenylacetates 5a, b with ethyl α-chloro-α-(methylthio) acetate (1) in the presence of stannic chloride gave the α-methylthio-1, 4-benzenediacetates 7a, b. The reactions of biphenyl, diphenylmethane, and diphenyl ether with an excess amount of 1 gave directly the corresponding disubstituted products 10a-c. Desulfurization of 7a, b and 10a-c gave the corresponding diacetates 8a, b and 11a-c. Methyl 4-(2-oxopropyl) phenylacetate (14) was prepared by reaction of methyl phenylacetate with α-chloro-α-(methylthio)acetone (2) followed by desulfurization of the resulting product. Methyl 2-(2-furyl)propionate (19) reacted with 2 in the presence of zinc chloride to give the 2, 5-disubstituted furan 20, whose desulfurization gave methyl 2-[5-(2-oxopropyl)-2-furyl]propionate (21).