Phenol → 2-(Ethylthio)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of phenol (87.5 g, 0.93 moles), xylene (100 ml), and zirconium tetrachloride (6.0 g, 0.026 moles) was heated to reflux under a slow nitrogen stream. The xylene was distilled through a 10 inch Vigreux column. The distillation was continued over a 2 hour period until the reaction mixture reached 177° C. Approximately 10 g of phenol was distilled with the xylene. The reaction mass was cooled to 150° C., and ethyl disulfide (62.0 g, 0.50 moles) was added. The reaction mixture was heated to 152° C., then heated slowly over a 5 hour period to 180° C., and finally held at 180° C. for an additional 10 hours. Ethyl mercaptan was removed continuously by distillation. The reaction mixture was cooled to 100° C., then vacuum distilled at 100 mm mercury until the pot temperature reached 200° C. to give 70.8 g of distillate. GC analysis indicated the distillate contained 34.0 g of ortho-(ethylthio)phenol (44% yield).

Provenance & Evidence