Benzoyl Peroxide → 4-tert-Butyltoluene

Participants

Reaction Conditions

Reaction Steps

N-Bromosuccinimide (98 g, 0.55 mol) and 0.5 g benzoyl peroxide were added to solution of 2-bromo-4-tert-butyl-1-methylbenzene (113.5 g, 0.5 mol) in CCl4 (500 ml). The resulting mixture was refluxed for 6 h, cooled to 20° C. and filtered. The resulting filtrate was evaporated and used without further purification. A solution of sodium diethylmethylmalonate, prepared from 104.5 g (0.6 mol) diethylmethylmalonate and 40.8 g of sodium ethylate in 500 ml abs. ethanol was treated dropwise with 2-bromo-1-(bromomethyl)-4-tert-butylbenzene (0.5 mol). The resulting mixture was refluxed for 4 h, treated with a solution of NaOH (50 g, 1.25 mol) in water (60 ml) and refluxed for 2 h, then poured into water (11), and finally washed with toluene (2×100 ml). The aqueous solution was treated with 130 ml of 35% HCl. The resulting mixture was extracted with chloroform (4×250 ml), the organic phase was dried over MgSO4 and evaporated. The residue was heated to 160-170° C. for 15 min yielding the product (92 g, total yield from 1-tert-butyl-4-methylbenzene 60%).

Provenance & Evidence