Diethyl Ether → 2,7-Di-tert-butyl-9H-thioxanthene

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Reaction Steps

The red oil obtained as described above from 12 g of bis-(4-t-butylphenyl)-sulfide was dissolved in 100 mL of dry ether, and the solution added dropwise over 15 min. to a suspension of 2.5 g of lithium aluminum hydride in 100 mL of dry ether while cooling in an ice bath. The mixture was refluxed for 3 hours, cooled and excess hydride destroyed by means of saturated ammonium chloride solution. The ether layer was washed with H2O and saturated NaCl solution, dried over MgSO4, and then evaporated to a white solid which was recrystallized from CH2Cl2 -hexane to give 9.0 g (72%) of the thioxanthene as white crystals, m.p. 152°-154°, 'H NMR (CDCl3) δ 1.28 (s, 18H, CH3), 3.84 (s, 2H, CH2), 7.31 (m, 6H, aryl). Anal. calculated for C21H26S: C, 81.23; H, 8.44; S, 10.33. Found: C, 81.45; H, 8.61; S, 10.24.

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