Hexane → 3-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

Participants

Reaction Steps

A 50% aqueous sodium hydroxide solution (65.0 g), tetrabutylammonium bromide (0.8 g, 2.5 mmol) and hexane (200 ml) were cooled with stirring in an ice bath. Compound 29 (16.32 g, 0.16 mol) and 1,6-dibromohexane (30) (100.00 g, 0.41 mol) were added and the reaction was left stirring until it reached room temperature; the reaction mixture was then heated under reflux for 3 h and then cooled to below 5° C. Water (300 ml) was added and the organic layer was retained and dried (Na2SO4). The drying agent was filtered off and the solvent was removed in vacuo. The resulting oil was purified by column chromatography [dichloromethane:hexane (1:6), to remove excess dibromohexane, dichloromethane, to isolate the product and then ethyl acetate to obtain the doubly reacted product) on silica.

Provenance & Evidence