Carbon Tetrachloride → 2-Chloro-4-(trifluoromethyl)phenol

HRID 365026Notes

Reaction equation

HRID 365026 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([O:9]C=CC)=[CH:5][CH:4]=1.OCC(CO)(CO)CO.C(Cl)(Cl)(Cl)[Cl:25]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:25][C:7]1[CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=[CH:5][C:6]=1[OH:9]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 8285PentaerythritolHCID 86740963Propenyl 4-trifluoromethylphenyl ether

Product 1

HCID 27366032-Chloro-4-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 0.5 mol of propenyl 4-trifluoromethylphenyl ether, 0.25 mol of pentaerythritol and 5 g of p-toluenesulphonic acid in 500 ml of carbon tetrachloride was stirred and refluxed under nitrogen for 40 minutes. The resulting solution was washed with 250 ml of water, and then dried by azeotroping 150 ml solvent in vacuo. After addition of 150 ml of fresh carbon tetrachloride, chlorine was passed into the solution for 2 hours, after which the solution was washed with 250 ml of water and the solvent was evaporated. The remaining product was purified by fractional distillation to give 74.8 g of 2chloro-4-trifluoromethylphenol, b.p: 52°-53.5° C. at 6 Torr., which was identified and shown by gas chromatography to have a purity of greater than 97%.

Workup

  1. temperaturerefluxed under nitrogen for 40 minutes
  2. washThe resulting solution was washed with 250 ml of water
  3. customdried
  4. customby azeotroping 150 ml solvent in vacuo
  5. additionAfter addition of 150 ml of fresh carbon tetrachloride, chlorine
  6. washafter which the solution was washed with 250 ml of water
  7. customthe solvent was evaporated
  8. distillationThe remaining product was purified by fractional distillation

Sources & evidence

ORD record
ord-601846c7f92a42eb92e807bb8f19e514
Source dataset
uspto-grants-1986_08
Patent number
US04607128

Reaction notes

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