Dimethyl Sulfate → HCID 21310391, compound

HRID 1740487Notes

Reaction equation

HRID 1740487 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

Procedure

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.

Workup

  1. customequipped with a reflux condenser
  2. temperaturethe temperature being maintained below 30° C
  3. customThe organic phase is separated
  4. washis washed with 0.5 l of water
  5. filtrationfiltered
  6. concentrationconcentrated by distillation under reduced pressure

Sources & evidence

ORD record
ord-4aa928829cde435ca0a2ff477e167a51
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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