Dimethylformamide → p-(3-Phenylpropylthio)acetophenone

HRID 259657Notes

Reaction equation

HRID 259657 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][SH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]1([CH2:7][CH2:8][CH2:9][S:10][C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 905963-Phenylpropane-1-thiol

Product 1

HCID 21422392p-(3-Phenylpropylthio)acetophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 174.6 grams (1.15 mole) of 3-phenylpropyl thiol, 158.8 grams (1.15 mole) of p-fluoroacetophenone and 158.8 grams (1.15 mole) of potassium carbonate in 500 ml. of dry dimethylformamide is stirred at its reflux temperature for approximately 24 hours. The reaction mixture is cooled, water added and extracted with methylene chloride. The extract is washed with water, a solution of 2 N sodium hydroxide, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue is recrystallized from isopropyl alcohol to yield the desired p-(3-phenylpropylthio)acetophenone having a m.p. of 76°-8° C.

Workup

  1. temperaturereflux temperature for approximately 24 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe extract is washed with water
  5. dry with materiala solution of 2 N sodium hydroxide, dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-4cec5fb0ee97485c9bd8bce822d61aa2
Source dataset
uspto-grants-1977_07
Patent number
US04038412

Reaction notes

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