Toluene → 2-t-Butyl-4-(3'-dimethylvinylsilylpropoxy)phenol

Participants

Reaction Conditions

Reaction Steps

A 500-mL, 3-neck flask fitted with mechanical stirring and an inert gas inlet topped reflux condenser, was charged with t-butylhydroquinone (BHQ) (25.0 g, 0.15 mol), 2-methoxyethanol (125 mL), water (125 mL) and potassium hydroxide pellets (9.5 g, 0.17 mol). The mixture was stirred under inert gas (argon; nitrogen could also be used) to effect solution, the chloropropyldimethyl-vinylsilane (25.0 g, 0.15 mol) was added in one portion. The red-amber solution was heated to the reflux temperature and was maintained at that temperature for 24 hours. The reaction mixture was cooled to 30° C., then poured into a separatory funnel containing saturated aqueous sodium chloride solution (100 mL) and toluene (200 mL). The reaction flask was washed with toluene (50 mL), and the washings were added to the separatory funnel. After vigorous agitation, the upper organic layer was separated. The lower aqueous layer was extracted with toluene (200 mL). The toluene fractions were combined and washed with water (3×100 mL), dried over anhydrous magnesium sulfate, filtered and stripped to oil (36.1 g) using a rotary evaporator (water aspirator, 70° C.). The oil was vacuum distilled (0.05 mm Hg). The product, I, was collected from 130° C. to 143° C., (28.9 g, 66% yield). It was 94.3% pure by G.C. The postulated structure of I was confirmed by IR and 1H NMR analyses.

Provenance & Evidence