P-Chloroacetophenone → HCID 22134085, compound

HRID 1439879Notes

Reaction equation

HRID 1439879 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=C[CH:2]=1.[C:8](=O)([O-])[O-].[K+].[K+].Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH3:22])=[CH:17][CH:16]=1>CN(C=O)C>[C:18]1([C:21]2[CH:22]=[CH:8][C:6]([C:1](=[S:7])[CH3:2])=[CH:5][CH:4]=2)[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 22134085HCID 22134085, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Thiophenol (184 g) was gradually added dropwise to a suspension of 196 g of anhydrous potassium carbonate in 1,000 ml of DMF at room temperature, followed by dropwise addition of 200 g of 4'-chloroacetophenone. The resultant mixture was stirred with heating overnight at 100° C. The reaction mixture was poured into 2,000 ml of ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. n-Hexane was added to the residue, and the resultant crystals were collected by filtration and washed with n-hexane. Thus was obtained 224 g of 4'-phenylthioacetophenone as crystals (m.p. 48°-50° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionn-Hexane was added to the residue
  6. filtrationthe resultant crystals were collected by filtration
  7. washwashed with n-hexane

Sources & evidence

ORD record
ord-1fc7e5475f574e23afe0939778b6c26d
Source dataset
uspto-grants-1996_03
Patent number
US05496844

Reaction notes

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