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Synthesis 1988; 1988(4): 303-306
DOI: 10.1055/s-1988-27549
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One-Pot Syntheses of Methyl p- and o-Hydroxydithiobenzoates from Phenol Ethers

R. Karl Dieter* , Ananda G. Lugade
  • *Howard L. Hunter Chemistry Laboratories, Clemson University, Clemson, SC 29634-1905, USA
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Publication Date:
20 August 2002 (online)

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Methyl p- and o-hydroxydithiobenzoates were prepared regiospecifically in a one-pot procedure from phenol methyl- and methoxymethyl, ethers, respectively. The p-hydroxy compounds were prepared by treatment of the methyl ethers with carbon disulfide, methyl iodide, and aluminum chloride. The second procedure involves ortho-metallation, carbon disulfide dithiocarboxylation, sulfur alkylation with methyl iodide, and in situ phenol deprotection with aluminum chloride/methyl iodide.