Ammonia → 1,3-Di-tert-butylbenzene

Participants

Reaction Conditions

Reaction Steps

To NH3 (liquid, 250 mL) was added a solution of phosphoric acid 2,4-di-tert-butyl-phenyl ester diethyl ester (51 g, crude from last step, about 0.2 mol) in Et2O (anhydrous, 150 mL) at −78° C. under N2 atmosphere. Lithium metal was added to the solution in small pieces until a blue color persisted. The reaction mixture was stirred at −78° C. for 15 min and then quenched with sat. NH4Cl solution until the mixture turned colorless. Liquid NH3 was evaporated and the residue was dissolved in water, extracted with Et2O (300 mL×2). The combined organic phases were dried over Na2SO4 and concentrated to give crude 1,3-di-tert-butyl-benzene as a yellow oil (30.4 g, 94% over 2 steps, contaminated with some mineral oil), which was used directly in next step.

Provenance & Evidence