Dimethyl Sulfate → HCID 18931223, compound

HRID 1598991Notes

Reaction equation

HRID 1598991 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[OH:17])[O:9][CH2:8][CH2:7][O:6]1.S(OC)(O[CH3:22])(=O)=O>CN(C=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:22])[O:9][CH2:8][CH2:7][O:6]1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 18931275HCID 18931275, compound

Product 1

HCID 18931223HCID 18931223, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-chloro-1-(5-chloro-2-hydroxyphenyl)-1,1-ethylenedioxybutane (0.86 g, 2.5 mmol) sodium hydride (0.18 g, 4.5 mmol in mineral oil) and DMF (3 mL) was stirred 30 minutes. The mixture was cooled to approximately 0° C. and dimethyl sulfate (0.44 g, 3.5 mmol) was added. The mixture was heated 4 hours with stirring at approximately 25° C. and then poured into ice cold water. The mixture was extracted with ether/pentane (7:3) and the extract concentrated to give 4-chloro-1-(5-chloro-2-methoxyphenyl)-1,1-ethylenedioxybutane (0.85 g, 2.4 mmol).

Workup

  1. temperatureThe mixture was heated 4 hours
  2. stirringwith stirring at approximately 25° C.
  3. additionpoured into ice cold water
  4. extractionThe mixture was extracted with ether/pentane (7:3)
  5. concentrationthe extract concentrated

Sources & evidence

ORD record
ord-386e65e57bfe4bd79a2ece9740a8b70d
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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