105077-08-5Relevant academic research and scientific papers
Syntheses of Arenediacetic Esters and Acetonyl-Substituted Arylacetic Esters by Means of Friedel-Crafts Reaction with α-Acyl-α-chlorosulfides
Ishibashi, Hiroyuki,Ikeda, Masazumi,Choi, Hong Dae,Nakagawa, Hiroko,Ueda, Yuko,Tamura, Yasumitsu
, p. 5310 - 5315 (2007/10/02)
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-propionate (21).Keywords - arenediacetic ester; Friedel-Crafts reaction; α-chlorosulfide; nonactic acid; nonactin; desulfurization; Raney nickel; stannic chloride; zinc chloride
