Water → 1-Phenylsulfonyl-1-acetyl-2-vinylcyclopropane

HRID 1248185Notes

Reaction equation

HRID 1248185 reaction equation
[C:1]1([S:7]([CH2:10][C:11](=[O:13])[CH3:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14](Cl)/[CH:15]=[CH:16]/[CH2:17]Cl.[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.O>S1(CCCC1)(=O)=O>[C:1]1([S:7]([C:10]2([C:11](=[O:13])[CH3:12])[CH2:17][CH:16]2[CH:15]=[CH2:14])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 735827PhenylsulfonylacetoneHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 155922191-Phenylsulfonyl-1-acetyl-2-vinylcyclopropane

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

Utilizing a phase-transfer procedure similar to that described in Example I, phenylsulfonylacetone was reacted with 1,4-dichlorobutene-2 to obtain 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane. For the reaction, 9.91 grams phenylsulfonylacetone (Parish Chemical Co.) and 6.25 grams 1,4-dichlorobutene-2 were combined in 20 mls sulfolane containing 6.6 grams potassium hydroxide (85%) and 5 mole percent tricaprylylmethylammonium chloride. The reaction mixture was stirred at 35°-40° C. for 31/2 hours. One-hundred mls water was then added to dissolve the white granular precipitate which had formed and the mixture extracted several times with ether. A crude red oil (10.8 grams) was obtained after removal of the ether and further work-up utilizing a Waters Preparatory Liquid Chromatograph 500A equipped with a gel permeation column and operated at a flow rate of 0.1 l/min yielded the cis and trans isomers of 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane. ##STR18## trans 1-phenylsulfonyl-1-acetyl-2-vinylcyclopropane

Workup

  1. dissolutionto dissolve the white granular precipitate which
  2. customhad formed
  3. extractionthe mixture extracted several times with ether
  4. customA crude red oil (10.8 grams) was obtained
  5. customafter removal of the ether and further work-up
  6. customequipped with a gel permeation column

Sources & evidence

ORD record
ord-9fc045320f50479daa8d083131114670
Source dataset
uspto-grants-1985_06
Patent number
US04522950

Reaction notes

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