Acetone → HCID 22118361, compound

HRID 1275432Notes

Reaction equation

HRID 1275432 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[SH:9].Cl[CH2:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14].CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9][CH2:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 776152,5-XylenethiolHCID 83542beta-Chloropivalic acid

Product 1

HCID 22118361HCID 22118361, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100-ml round-bottomed flask was charged with 1.38 g (10.00 mmol) of 2,5-dimethylthiophenol, 1.40 g (10.26 mmol) of 3-chloropivalic acid and 15 ml of acetone. Then, 2.07 g (15.0 mmol) of potassium carbonate was added, and the mixture was refluxed under heat for 30 minutes. The reaction mixture was allowed to cool to room temperature, and then about 100 ml of water was added. An aqueous layer was washed with n-hexane once, and neutralized and acidified with a 5 wt % hydrochloric acid aqueous solution. A precipitated solid was extracted with ethyl acetate, and an organic layer was washed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 1.90 g (yield 80%) of 3-(2,5-dimethylphenylthio)pivalic acid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 30 minutes
  3. washAn aqueous layer was washed with n-hexane once
  4. extractionA precipitated solid was extracted with ethyl acetate
  5. washan organic layer was washed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c70de4ae941b4685962564f4d8239667
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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