4-Chlorophenol → 1-(4-Chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-one

HRID 1995924Notes

Reaction equation

HRID 1995924 reaction equation
Br[CH2:2][C:3](=[O:16])[C:4]([CH3:15])([CH3:14])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:2][C:3](=[O:16])[C:4]([CH3:15])([CH3:14])[CH2:5][S:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 127659741-Bromo-4-[(4-chlorophenyl)sulfanyl]-3,3-dimethylbutan-2-one

Product 1

HCID 127659751-(4-Chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

133.7 g (0.41 mol) of 1-bromo-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-one were heated to 100° C. with 64 g (0.5 mol) of 4-chlorophenol and 69 g (0.5 mol) of potassium carbonate in 500 ml of toluene for 5 hours. The mixture was then allowed to cool and was filtered. The filtrate was extracted by shaking with dilute sodium hydroxide solution, rinsed with water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. 110.5 g (72% of theory) of 1-(4-chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-butan-2-one were obtained as a yellowish oil with a refractive index nD20 of 1.5932.

Workup

  1. temperatureto cool
  2. filtrationwas filtered
  3. extractionThe filtrate was extracted
  4. washrinsed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent in vacuo

Sources & evidence

ORD record
ord-075536da7058404898563a466240b214
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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