M-Cresol → HCID 21430249, compound

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Reaction Steps

To a solution of 22.4 g. (0.21 mole) of m-cresol in 100 ml. of carbon tetrachloride is added dropwise with stirring, 30.0 g. (0.21 mole) of phenyl sulfenyl chloride at 0°-5° C. over a period of 30 minutes. The light pink solution is stirred overnight at room temperature and then concentrated in vacuo to give 44.8 g. of the impure phenol. The crude product is taken up in 100 ml. of 10% sodium hydroxide, and extracted twice with 50 ml. portions of ether, which are discarded. The basic solution is neutralized with concentrated hydrochloric acid and then extracted twice with 50 ml. portions of chloroform. The organic extracts are combined, dried over sodium sulfate and concentrated in vacuo to give 34.9 g. of yellow oil. Fractional distillation yields 19.9 g. (b.p. 125°-135° C./ 0.1 mm) of the desired phenol.

Provenance & Evidence