Dimethyl Sulfate → HCID 12256606, compound

HRID 1975349Notes

Reaction equation

HRID 1975349 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.S(OC)(O[CH3:15])(=O)=O.[OH-].[Na+]>>[CH3:15][S:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][Cl:1])=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 12256596HCID 12256596, compound

Product 1

HCID 12256606HCID 12256606, compound

Procedure

The starting material is prepared as follows: (a) 64.3 g of 4-chloroethylthiophenol are placed in a vessel with 13.3 g of dimethyl sulfate; with external cooling (IT<10°), 41 ml of NaOH (25%) are then slowly added dropwise. After approximately one hour, the external cooling is removed and the mixture is heated carefully and kept at 125° for 30 minutes. The cooled solution is extracted with ether and distilled, yielding 4-methylmercaptophenylethyl chloride; b.p. 94°-95°/0.1 mbar.

Workup

  1. customThe starting material is prepared
  2. additionare then slowly added dropwise
  3. temperaturethe external cooling
  4. customis removed
  5. temperaturethe mixture is heated carefully
  6. waitkept at 125° for 30 minutes
  7. extractionThe cooled solution is extracted with ether
  8. distillationdistilled

Sources & evidence

ORD record
ord-956b61c9da474b6f8332dcae52156648
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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