Water → 4-tert-Butyl-2-(trifluoromethyl)phenol

HRID 598725Notes

Reaction equation

HRID 598725 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[C:12](O)([CH3:15])([CH3:14])[CH3:13].OS(O)(=O)=O.O>C(O)(C(F)(F)F)=O>[C:12]([C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:8]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 679582-Trifluoromethylphenol

Product 1

HCID 126521024-tert-Butyl-2-(trifluoromethyl)phenolYield 50.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Trifluoromethyl-phenol (2.98 g, 18.3 mmol) was dissolved in 12 mL TFA and t-butanol (1.43 g, 19.3 mmol) and H2SO4 (0.24 mL) were added. The reaction was stirred at rt for 48 hrs, after which water was added and the compound was extracted into DCM. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (2/1 Hex/EtOAc) to yield 2.01 g of the target compound.

Workup

  1. extractionthe compound was extracted into DCM
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (2/1 Hex/EtOAc)

Sources & evidence

ORD record
ord-cd587d57c3484f91be5f660b795b7ade
Source dataset
uspto-grants-2011_03
Patent number
US07897599B2

Reaction notes

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