Aluminum → 2,4-Di-tert-butyl-6-(trifluoromethyl)phenol

HRID 2351114Notes

Reaction equation

HRID 2351114 reaction equation
[Al].[C:2]([C:6]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:9](=[O:16])[C:8](O)([C:17]([F:20])([F:19])[F:18])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3]>O>[C:12]([C:10]1[CH:11]=[C:6]([C:2]([CH3:3])([CH3:4])[CH3:5])[CH:7]=[C:8]([C:17]([F:19])([F:20])[F:18])[C:9]=1[OH:16])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 14343503HCID 14343503, compound

Product 1

HCID 143435082,4-Di-tert-butyl-6-(trifluoromethyl)phenolYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A strip of aluminum foil weighing 293 mg (11 mmol) was amalgamated by immersion in a solution of 2% mercuric chloride in water for 15 sec., washed with absolute ethanol followed by diethyl ether, cut into small pieces, and added to a solution of 315 mg (1.1 mmol) of 4,6-di-tert-butyl-2-hydroxy-2-trifluoromethyl-3,5-cyclohexadien-1-one in 25 mL of 10% water--90% tetrahydrofuran. The resulting mixture was heated at 60°-70° C. for 2 hours, allowed to cool to room temperature, and filtered. The filter cake was washed with diethyl ether. Concentration of the combined filtrates gave a residue which was poured into 10 mL of water. The aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying, and concentration of the organic layers gave a residue which was purified by PTLC (one 2 mm silica gel plate eluted with petroleum ether), affording 218 mg (73% yield) of 2,4-di-tert-butyl-6-trifluoromethylphenol.

Workup

  1. wash, washed with absolute ethanol
  2. temperatureThe resulting mixture was heated at 60°-70° C. for 2 hours
  3. filtrationfiltered
  4. washThe filter cake was washed with diethyl ether
  5. customConcentration of the combined filtrates gave a residue which
  6. extractionThe aqueous mixture was extracted with three 10 mL portions of dichloromethane
  7. customCombination, drying
  8. customconcentration of the organic layers gave a residue which
  9. customwas purified by PTLC (one 2 mm silica gel plate eluted with petroleum ether)

Sources & evidence

ORD record
ord-d8373fd58b314da78672ccd8a446eb50
Source dataset
uspto-grants-1989_10
Patent number
US04871877

Reaction notes

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