Carbon Tetrachloride → HCID 23036213, compound

HRID 1194729Notes

Reaction equation

HRID 1194729 reaction equation
C[C:2]1[CH:9]=[CH:8][C:5](CO)=[CH:4][C:3]=1[C:10]([Cl:14])=[C:11]([Cl:13])Cl.[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]([Cl:38])(Cl)(Cl)[Cl:35]>>[CH3:15][C:8]1[CH:9]=[CH:2][C:3]([CH:10]([Cl:14])[C:11]([Cl:13])=[C:34]([Cl:38])[Cl:35])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 20154054HCID 20154054, compound

Product 1

HCID 23036213HCID 23036213, compound

Procedure

A solution of 4-methyl-3-(trichlorovinyl)benzyl alcohol (2.06 g) and triphenylphosphine (2.58 g) in 100 ml of carbon tetrachloride was heated at reflux for 48 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in CH2Cl2 (200 ml). This organic solution was shaken with 30% H2O2 (10 ml) and then diluted with water (100 ml) and the layers separated. The organic layer was further washed with water, dried with anhydrous magnesium sulfate and concentrated to give 4.37 g of crude product. Chromatography on silica (1:1 hexane:methylene chloride) gave 1.81 g of 4-methyl-(trichlorovinyl)benzyl chloride.

Workup

  1. temperatureat reflux for 48 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in CH2Cl2 (200 ml)
  4. additiondiluted with water (100 ml)
  5. customthe layers separated
  6. washThe organic layer was further washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give 4.37 g of crude product

Sources & evidence

ORD record
ord-36c4315c78774b7dbcd63b9add28f3d3
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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