Dichloromethane → HCID 86642025, compound

Participants

Reaction Steps

Dichloromethane (25 mL), 2-[(1,5-dimethylhexyl)oxy]ethanol (5 g, 29 mmol), a solution of potassium bromide (0.34 g, 2.9 mmol) in water (4.72 g) and 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO, 0.053 g, 0.34 mmol) was charged to 100 mL flask fitted with addition funnel, condenser, nitrogen, thermocouple and mechanical stirrer. A 2.8 wt % aqueous solution of sodium hypochlorite (173.5 g, 65 mmol) was added and the reaction stirred for a total of 15 hrs. The product was extracted with hexane (200 ml) and washed with water (2×200 ml). The organic phase was dried over sodium sulphate, filtered and the solvent removed by evaporation to yield a colourless oil (3.9 g). This oil (2 g) was chromatographed over silica gel (methyltert-butyl ether/hexane) to yield the product as a colourless oil (1.18 g, equating to a total chemical yield of 25%).

Provenance & Evidence