Dimethyl Sulfoxide → HCID 64764771, compound

Participants

Reaction Steps

To a solution of 60.1 g (0.40 mol) 2-tert-butylphenol in 600 ml of DMSO 89.6 g (1.60 mol) of KOH and 147 g (0.80 mol) of isobutyl iodide were added. This mixture was stirred for 2 h at room temperature, then 73.6 g (0.40 mol) of isobutyl iodide was added. The resulting mixture was stirred for 1 h, and, again, then 73.6 g (0.40 mol) of isobutyl iodide was added. The formed mixture was stirred overnight at room temperature. The top layer was separated. To the bottom layer 5 liters of water was added, and some product was extracted with 2×250 ml of dichloromethane. The combined organic extract (including the separated top layer) was washed with 5×1 liter of water, dried over Na2SO4, and evaporated to dryness. The crude product (free of 2-tert-butylphenol) was obtained from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes). Further on, this crude product was distillated to give pure 1-tert-butyl-2-isobutoxybenzene, b.p. 85-95° C./4 mm Hg. This procedure gave 44.9 g (54%) of the title product.

Provenance & Evidence