Dimethyl Sulfate → HCID 21310391, compound

Participants

Reaction Steps

420 ml of demineralized water and 420 g (10.5 mol) of sodium hydroxide pellets are introduced into a 6-liter reactor equipped with a reflux condenser, a temperature probe and a dropping funnel. 2.3 1 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 benzyltriethyl ammonium chloride are added to the stirred solution at 20° C. 567 g (4.50 mol) of dimethyl sulphate are then added over 50 min, the temperature being maintained below 30° C. The mixture is stirred for 18 hours and then 1 liter of water is added. The organic phase is separated and is 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