Isopropyl iodide → HCID 14687427, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 15.5 g of 4-nitrocatechol (100 mmol) in 200 ml of N,N-dimethylformamide is added dropwise at 0° C. to a 60% suspension of sodium hydride in oil (4.2 g, 105 mmol). At the end of the addition (1 hour), the dark red solution is stirred at 0° C. for 1.5 hours and 10.5 mnl of 2-iodopropane (105 mmol) are then added dropwise. The mixture is then brought to 80° C. and stirred for 16 hours. It is then cooled to room temperature, the solvent is evaporated off and the dark red oil is dissolved in dichloromethane (300 ml). The solution is washed with water and then with saturated aqueous sodium chloride solution, the organic phase is dried over sodium sulfate and filtered, and the solvent is evaporated off. The expected product is isolated by chromatography on a column of silica (eluent: 80/20 cyclohexane/ethyl acetate). 10.5 g of a yellow oil which solidifies are recovered:

Provenance & Evidence