p-Toluenesulfonic acid → 11-Bromo-1-tetrahydropyranyloxyundecane

Participants

Reaction Conditions

Reaction Steps

50 g (0.199 mol) of 11-bromo-1-undecanol (Aldrich) was dissolved in 500 ml of dichloromethane, and the mixture was cooled to 0° C. 22.15 ml (0.242 mol) of dihydropyran were added dropwise over a period of two hours; the reaction was started by addition of a few crystals of p-toluenesulphonic acid at the beginning of the addition. After the addition was complete, the reaction mixture was stirred for 15 min and stopped by addition of 0.5 g of NaHCO3. After evaporation of the dichloromethane, the pale yellow syrup obtained was dissolved in ethyl acetate and purified by filtration through silica gel. Yield=65.3 g (98%).

Provenance & Evidence