Diphenyl sulfide → 1,1'-Sulfanediylbis(4-tert-butylbenzene)

Participants

Reaction Steps

To a mixture of 93 g of phenyl sulfide, 92.5 g of t-butyl chloride and 200 mL of CS2 cooled in an ice bath, 133 g of AlCl3 was added over a period of 1 hour. Following complete addition, the mixture was allowed to warm slowly to room temperature and stirred overnight. The mixture was subjected to decomposition with ice, extraction with ether and washing of the ether solution successively with water, 5% NaHCO3, water and saturated NaCl solution and gave after evaporation of dried (MgSO4) extracts, a solid which upon crystallization from methanol gave 145 g (97%) of the sulfide as white crystals, m.p. 83-84; 'H NMR (CDCl3) δ 1.32 (s, 18H, CH3), 7.35 (s, 8H, aryl).

Provenance & Evidence