Hydrochloric Acid → o-(Methylthio)phenol

Temperature

150 °C

Zirconium tetrachloride (23.4 g, 0.1 mole) was added to phenol (141.2 g, 1.5 moles). The mixture was slowly heated to 150° C. under nitrogen and maintained at this temperature for 12 hours during which HCl was allowed to escape. The mixture was cooled to ca. 100° C. and methyl disulfide (94.2 g, 1 mole) was added. The mixture was heated under nitrogen for 15 hours during which temperature was increased slowly to 159° C. Methyl mercaptan was allowed to escape continuously. Distillation of the mixture at 1.4 mm mercury to a maximum head temperature of 113° C. yielded 125.6 g of distillate. GC analysis indicated the distillate contained 59.1 g of phenol (42% recovered) and 54.2 g of ortho-(methylthio)phenol (39% yield). The unreacted phenol was removed from the distillate by fractional distillation through a 12 cm glass helices packed column. The remaining material was fractionally distilled through a 5 inch Vigreux column yielding a main fraction of 99.6% pure ortho-(methylthio)phenol distillating at 112°-114° C. at 30 mm mercury.

1. temperatureThe mixture was cooled to ca. 100° C.
2. temperatureThe mixture was heated under nitrogen for 15 hours during which temperature
3. temperaturewas increased slowly to 159° C
4. distillationDistillation of the mixture at 1.4 mm mercury to a maximum head temperature of 113° C.
5. customyielded 125.6 g of distillate

ORD record

ord-a8ed944e86734821bd529993fac96318

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599451