Dichloromethane → 2,7-Di-tert-butyl-9H-thioxanthen-9-one

Participants

Reaction Steps

To a mixture of 12 g of bis-(4-t-butylphenyl)-sulfide, 100 mL of dry CH2Cl2 and 21 g of SnCl4 cooled in an ice bath for a period of 30 min., a solution of 9.27 g of α,α-dichloromethyl methyl ether in 50 mL of CH2CH2 was added dropwise. After addition was complete, a deep red mixture was obtained which was allowed to warm slowly to room temperature, stirred for 2 hours and then slowly poured into water. Extraction with CHCl3, followed by washing of the extracts successively with H2O, 5% NaHCO3, H2O and saturated NaCl solution, drying over (MgSO4), and evaporation of solvent gave a red oil which was chromatographed on silica gel. Elution by means of hexane-ethyl acetate (95/5) removed 4.6 g (37% of 2,7-di-t-butylthioxanthene after which there was obtained 4.65 g (37%) of the ketone which was recrystallized from hexane --CH2Cl2 as yellow crystals, m.p. 176°-178°, 'NMR (CDCl3) δ 1.35 (s, 18H, CH3), 7.5 (m, 4H, aryl), 8.75 (d, 2H, CHCCO). Anal. calculated for C21H24OS: C, 77.73; H, 7.46; S, 9.88. Found C, 77.83; H, 7.58; S, 9.75.

Provenance & Evidence