Dimethyl Sulfate → HCID 21556730, compound

HRID 267289Notes

Reaction equation

HRID 267289 reaction equation
[Br:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([SH:11])=[C:4]([CH:12]([CH3:14])[CH3:13])[CH:3]=1.[OH-].[Na+].[CH3:17]OS(OC)(=O)=O>O>[CH3:17][S:11][C:5]1[CH:6]=[C:7]([CH:8]([CH3:9])[CH3:10])[C:2]([Br:1])=[CH:3][C:4]=1[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 215567424-Bromo-2,5-di(propan-2-yl)benzene-1-thiol

Product 1

HCID 21556730HCID 21556730, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 78.4 g of 4-bromo-2,5-diisopropylbenzenethiol and 12.8 g of sodium hydroxide was stirred together in 200 ml of water while 50.4 g of dimethylsulfate was added at a rate to maintain the reaction temperature between 45°-55°C. After stirring for 3 hours at ambient temperature, the reaction mixture was extracted with ether. The ether solution, washed with half saturated sodium chloride solution and dried over sodium sulfate, was concentrated to an oil which was distilled to give 64 g of 4-bromo-2,5-diisopropylphenyl methyl sulfide, boiling at 91°-93°C at 0.15-0.1 mm Hg; ND23 1.5714.

Workup

  1. additionwas added at a rate
  2. temperatureto maintain the reaction temperature between 45°-55°C
  3. extractionthe reaction mixture was extracted with ether
  4. washThe ether solution, washed with half saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationwas concentrated to an oil which
  7. distillationwas distilled

Sources & evidence

ORD record
ord-a802feb0e0ed46c8b18bf7b3216e1a27
Source dataset
uspto-grants-1976_03
Patent number
US03941826

Reaction notes

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