Dimethyl Sulfate → HCID 21310391, compound

Participants

Reaction Conditions

Reaction Steps

420 ml of demineralized water and 420 g (10.5 mol) of sodium hydroxide pellets are introduced into a 6-liter reactor fitted with a condenser, a temperature probe and a dropping funnel. 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 are added to the solution with stirring at 20° C. 567 g (4.50 mol) of dimethyl sulphate are then added over 50 minutes while maintaining 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 off 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