Thiophenol → 4-Tert-Butylbenzenethiol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1285 grams (5.8 moles) of tert-butyl 4-(tert-butyl)phenyl sulfide (from replicates of EXAMPLE III) 1040 grams (9.5 moles) of thiophenol, and 350 grams of boron trifluoride-phosphoric acid complex was heated slowly to 90° C. The reaction mixture was stirred at 90° C. for four hours, cooled to 25° C., the organic layer was separated from the lower catalyst layer and added to 500 ml of toluene. This toluene solution was washed five times with 1000-ml portions of water, dried with magnesium sulfate, and then concentrated in vacuo. The residue was distilled through a 10-tray column to give 1250 grams (65% yield) of p-(tert-butyl)thiophenol, b.p. 58°-60°/1.0 mm. The nmr spectrum supported the proposed structure. A residue of 285 grams of 4-(tert-butyl)phenyl tert-butyl sulfide was obtained.

Provenance & Evidence