Dimethyl Sulfate → HCID 21310391, compound

HRID 1856818Notes

Reaction equation

HRID 1856818 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:11])[O:8][C@H:7]([CH2:9][OH:10])[CH2:6][O:5]1.S(OC)(O[CH3:16])(=O)=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.ClCCl>[CH3:16][O:10][CH2:9][C@@H:7]1[CH2:6][O:5][C:4]([CH3:11])([CH3:3])[O:8]1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 736056(R)-Solketal

Product 1

HCID 21310391HCID 21310391, compoundYield 113.1%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

In 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 in pellets. To the solution, stirred at 20° C., are added 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 benzyltriethylammonium chloride. 567 g (4.50 mol) of dimethyl sulfate are then added in 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 1 of water. The aqueous phases are re-extracted with 3 1 of dichloromethane and the organic phases are then combined, filtered and concentrated by distillation under reduced pressure. 496 g of product are obtained.

Workup

  1. customIn a 6 liter reactor equipped with a condenser
  2. customthe temperature below 30° C
  3. stirringThe mixture is stirred for 18 hours
  4. customThe organic phase is separated
  5. washwashed with 0.5 1 of water
  6. extractionThe aqueous phases are re-extracted with 3 1 of dichloromethane
  7. filtrationfiltered
  8. concentrationconcentrated by distillation under reduced pressure

Sources & evidence

ORD record
ord-207333c9e94f4107aeaf8221658d692e
Source dataset
uspto-grants-2000_11
Patent number
US06143772

Reaction notes

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