Ammonia → Toluene

Participants

Reaction Conditions

Reaction Steps

To a slurry of benzyl alcohol of Example 8 (25.0 g, 0.044 moles) in toluene (250 ml), was added methanesulfonic anhydride (10.77 g, 0.062 moles) then cooled to 5° C. Triethylamine (6.93 g, 0.068 moles) was added over 30 minutes and stirred at this temperature for 3 hours. The resultant solution was added to 7M ammonia in methanol solution (316 ml, 2.21 moles) and stirred for 16 hours. Water (250 ml) was added and the organic phase washed with water (250 ml). The aqueous phases were extracted with toluene (125 ml) and the combined organics were dried by azeotropic distillation under reduced pressure to leave the title compound as a clear brown solution in toluene (125 ml) (assumed quantitative yield).

Provenance & Evidence