An improved synthesis of methyl p-hydroxyphenylalkanoates |
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| Authors: | Hong Dae Choi Yong Sil Kowak Dek Hyun Geum Byeng Wha Son |
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| Institution: | 1. Department of Chemistry, Dongeui University, 614-714, Pusan, Korea
2. Department of Chemistry, National Fisheries University of Pusan, 608-023, Pusan, Korea
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| Abstract: | Friedel-Crafts reaction of isopropoxybenzene with methyl α-chloro-α-(methylthio)acetate1 afforded methyl α-methylthio-p-isopropoxyphenylacetate2d, which was readily converted into methyl p-isopropoxyphenylacetate3 by reductive desulfurization with zinc dust in acetic acid. Methylation of3 with sodium hydride and methyl iodide gave methyl α-(p-isopropoxyphenyl)propionate5. Methyl p-hydroxyphenylalkanoates (4, 6), useful intermediates for some medicines, were easily prepared by treatment of3 and5 with titanium tetrachloride, respectively. |
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