Sulfuric Acid → 4-(Trifluoromethyl)phenol

HRID 365025Notes

Reaction equation

HRID 365025 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.S(=O)(=O)(O)O>CO>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([OH:9])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86740963Propenyl 4-trifluoromethylphenyl ether

Product 1

HCID 678744-(Trifluoromethyl)phenolYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 60.0 g of propenyl 4-trifluoromethylphenyl ether, 350 ml of methanol and aqueous sulphuric acid (20 ml 98% H2SO4 in 50 ml water) was refluxed for 4 hours. After dilution with 1200 ml water, the product was extracted twice with toluene. Removal of solvent and distillation of the residue gave 33.43 g of 4-trifluoromethylphenol, b.p.: 63°-64° C. at 6 Torr.

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionAfter dilution with 1200 ml water, the product was extracted twice with toluene
  3. customRemoval of solvent and distillation of the residue

Sources & evidence

ORD record
ord-81a9668c39cc407cbccb7af6b9cfaa04
Source dataset
uspto-grants-1986_08
Patent number
US04607128

Reaction notes

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