Water → 1-(3-Chloroprop-1-en-1-yl)-4-methylbenzene

HRID 1093508Notes

Reaction equation

HRID 1093508 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH2:10]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31]N1C(=O)CCC1=O.O>C(Cl)Cl>[Cl:31][CH2:10][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776Triphenylphosphine2×HCID 31398Chlorosuccinimide2×HCID 3611722-Propen-1-ol, 3-(4-methylphenyl)-, (2E)-

Product 1

HCID 542056751-(3-Chloroprop-1-en-1-yl)-4-methylbenzeneYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 102-1 (2.50 g) was dissolved in methylene chloride (60 ml), triphenylphosphine (4.86 g) and N-chlorosuccinimide (2.84 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr. Triphenylphosphine (4.86 g) and N-chlorosuccinimide (2.84 g) were further added, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride and washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate) to give the object product (1.20 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. stirringthe mixture was stirred for 1 hr
  4. extractionthe mixture was extracted with methylene chloride
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. additionDiethyl ether (100 ml) was added
  9. filtrationthe precipitated triphenylphosphine oxide was filtered off
  10. concentrationThe concentrate of the filtrate
  11. customwas purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-35dcecda85a148e2964a6e9301bf3759
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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