Water → 1-(3-Chloro-1-propenyl)-3-methylbenzene

HRID 1093511Notes

Reaction equation

HRID 1093511 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 536846413-(3-Methylphenyl)-2-propene-1-ol

Product 1

HCID 538233951-(3-Chloro-1-propenyl)-3-methylbenzeneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 103-1 (2.00 g) was dissolved in methylene chloride (45 ml), triphenylphosphine (3.89 g) and N-chlorosuccinimide (1.98 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 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=100:0-95:5) to give the object product (1.30 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionDiethyl ether (100 ml) was added
  8. filtrationthe precipitated triphenylphosphine oxide was filtered off
  9. concentrationThe concentrate of the filtrate
  10. customwas purified by silica gel column chromatography (hexane:ethyl acetate=100:0-95:5)

Sources & evidence

ORD record
ord-8be636a4a3da45668c9169f69bc1491c
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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