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Synthesis 1989; 1989(4): 253-255
DOI: 10.1055/s-1989-27215
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Carboxyalkylthiomethylation of Phenols

D. J. R. Massy* , A. Mckillop
  • *School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ, England
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Publication Date:
17 September 2002 (online)

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The syntheses of carboxyalkylthiomethyl-substituted phenols, 2.4-, 2,6- and 3,5-xylenols and 2,3,5,6-tetramethylphenol are described. In all cases except 2,6-xylenol, a one-step process based on refluxing the phenol with formalin and the sodium salt of a mercaptoalkanoic acid gave products substituted in all of the vacant ortho and para positions. With 2,6-xylenol a two-step process was necessary. The products are of interest as potential inhibitors of ferrous corrosion.