Thionyl Chloride → HCID 9992887, compound

HRID 1657278Notes

Reaction equation

HRID 1657278 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)([CH2:11][CH:12]=[CH2:13])[C:8](O)=[O:9])=[CH:3][CH:2]=1.S(Cl)(Cl)=O>CN(C)C=O.C(Cl)Cl>[C:17]1([CH3:20])[CH:18]=[CH:19][C:14]([C:7]2([C:4]3[CH:5]=[CH:6][C:1]([CH3:21])=[CH:2][CH:3]=3)[C:8](=[O:9])[CH:13]=[CH:12][CH2:11]2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 10333880HCID 10333880, compound

Product 1

HCID 9992887HCID 9992887, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-bis(p-tolyl)-4-pentenoic acid (8.17 g) in N,N-dimethylformamide (1.0 ml) and methylene chloride (45 ml) was added thionyl chloride (3.2 ml), and the solution was stirred at room temperature for 1 day. The solution was evaporated in vacuo and the residue was dissolved in methylene chloride (50 ml). The solution was added dropwise to a suspension of aluminum chloride (4.66 g) in methylene chloride (50 ml) with dry ice-acetone bath cooling under nitrogen atmosphere, and the resulting mixture was stirred at room temperature overnight. The mixture was poured into cooled 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, water, 1N sodium hydroxide, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (10:1~5:1) as an eluent to give 5,5-bis(p-tolyl)-2-cyclopenten-1-one (2.30 g).

Workup

  1. customThe solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride (50 ml)
  3. additionThe solution was added dropwise to a suspension of aluminum chloride (4.66 g) in methylene chloride (50 ml) with dry ice-acetone bath
  4. temperaturecooling under nitrogen atmosphere
  5. stirringthe resulting mixture was stirred at room temperature overnight
  6. additionThe mixture was poured
  7. temperatureinto cooled 1N hydrochloric acid
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with 1N hydrochloric acid, water, 1N sodium hydroxide, and brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in vacuo
  12. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (10:1~5:1) as an eluent

Sources & evidence

ORD record
ord-76bc421720b349d78a2397f11d208c8b
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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