Dimethyl Sulfate → HCID 21310391, compound

Participants

Reaction Conditions

Reaction Steps

Into a 6 liter reactor equipped with a condenser, a temperature probe and a dropping funnel are introduced 420 ml of demineralized water and 420 g (10.5 mol) of sodium hydroxide pellets. To the solution, stirred at 20° C., are added 2.3 l of dichloromethane, 396 g (3.00 mol) of (R)-2,2-dimethyl-1,3-dioxolane-4-methanol ([α]D20 =-11°; c=4; methanol) and 20.5 g (0.090 mol) of benzyltriethylammonium chloride. 567 g (4.50 mol) of dimethyl sulfate are then added in the course of 50 min, while keeping the temperature below 30° C. The mixture is stirred for 18 hours and then 1 liter of water is added. The organic phase is separated and washed with 0.5 l of water. The aqueous phases are reextracted with 3 l of dichloromethane and then the organic phases are combined, filtered and concentrated by distillation under reduced pressure. 496 g of product are obtained.

Provenance & Evidence