Abstract
THE alkaline hydrolysis of triphenylmethyl thiobenzoate or α-benzoylbenzhydryl thiobenzoate1 in alcoholic sodium hydroxide gave the corresponding thiol and benzoic acid, Ph.COSR + NaOH → Ph.COONa + R.SH. But the acid hydrolysis of triphenylmethyl thiobenzoate (1·2 gm. in 200 c.c. alcohol and 30 c.c. conc. hydrochloric acid and boiled for 15 minutes) gave triphenylmethyl carbinol and thiobenzoic acid (separated and identified by oxidation to the disulphide):
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References
Schönberg and Iskander, J. Chem. Soc., 92 (1942).
J. Chem. Soc., 444 (1940).
Cf. Annual Report Chem. Soc., 229 (1940).
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ISKANDER, Y. Hydrolysis of Thioesters. Nature 155, 141 (1945). https://doi.org/10.1038/155141c0
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DOI: https://doi.org/10.1038/155141c0
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