Hydrochloric Acid → 2-(Ethylthio)phenol

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Zirconium tetrachloride (23.4 g, 0.1 mole) was added to phenol (141.2 g, 1.5 moles). The mixture was slowly heated to 156° C. under nitrogen and maintained at this temperature overnight while allowing HCl to escape. The mixture was cooled to ca. 100° C. and ethyl disulfide (122.3 g, 1 mole) was added. The mixture was heated under nitrogen while ethyl mercaptan was removed continuously by distillation. Heating was continued for a total of 7 hours during which temperature slowly increased to 198° C. Distillation of the mixture at 0.4 mm mercury to a maximum head temperature of 101° C. yielded 134.7 g of distillate. GC analysis indicated the distillate contained 53.4 g of phenol (38% recovered) and 63.7 g of ortho-(ethylthio)phenol (41% yield). Fractional distillation through a 5 inch Vigreux column yielded, after removal of phenol, a main fraction of 99.2% pure ortho-(ethylthio)phenol distilling at 125°-127° C. at 30 mm mercury.

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