tert-Butanol → 1,1-Dimethylethyl 4-methylbenzoate

Reaction equation

[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([C:17](Cl)=[O:18])=[CH:13][CH:12]=1>C(OCC)C>[C:1]([O:5][C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:20])=[CH:12][CH:13]=1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

Procedure

A 1 L three-neck flask fitted with a reflux condenser, rubber septum, addition funnel and argon inlet was charged with 200 ml of t-butanol. To the solution, n-butyl lithium (1.45N, 91.1 ml) was added dropwise using a water bath to prevent an excessive temperature rise. After stirring 30 minutes, the addition funnel was charged with p-toluoyl chloride, added dropwise. The reaction mixture was stirred overnight. At this point, the contents were transferred into a separatory funnel by using 250 ml of diethyl ether and the solution was washed with water (250 ml). The organic layer was then dried (MgSO4) and concentrated by rotary evaporation. The crude product, tert-butyl-4-toluate, was purified by fractional distillation.