Sulfuric Acid → tert-Butyl 4-iodobutanoate

Participants

Reaction Steps

To a solution of concentrated sulfuric acid (2 ml) and 1,4-dioxane (20 ml) in a pressure bottle at 0° C. were added 4-iodobutanoic acid (5.5 g, 25.7 mmol) and isobutene (30 ml). The mixture was stirred at room temperature for 3 days, cooled to 0° C. and poured slowly into an aqueous solution (120 ml) of sodium bicarbonate (10 g). The mixture was stirred at room temperature for 15 minutes and extracted with diethyl ether. The organic phase was washed three times with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:dichloromethane=1:1) to give the title compound (4.24 g, 61%) as a pale yellow liquid.

Provenance & Evidence