Phenol → o-(Methylthio)phenol

Participants

Reaction Steps

Phenol (12.5 g, 0.13 moles), methyl disulfide (8.4 g, 0.089 moles), and H ELZ-20 (2.5 g) were combined and heated under nitrogen at reflux for 3 hours during which the temperature increased to 180° C. and GC analysis indicated no further increase in the amount of ortho-(methylthio)phenol. Methyl mercaptan was allowed to escape continuously. The mixture was cooled to room temperature and filtered. The catalyst was washed several times with ether and allowed to dry leaving solid weighing 3.2 g. The filtrate and ether washings were combined, and volatiles were removed on a rotary flash evaporator leaving 15.2 g of liquid. GC analysis indicated the presence of phenol (5.3 g, 43% recovered), ortho-(methylthio)phenol (5.1 g, 41% yield), para-(methylthio)phenol (2.3 g), and di(methylthio)phenols (2.2 g).

Provenance & Evidence