Sulfuric Acid → 2-(Hydroxymethyl)-4-(trifluoromethyl)phenol

HRID 1081876Notes

Reaction equation

HRID 1081876 reaction equation
COC[O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:6]=1[CH2:7][OH:8].OS(O)(=O)=O>CO>[OH:8][CH2:7][C:6]1[CH:9]=[C:10]([C:13]([F:15])([F:16])[F:14])[CH:11]=[CH:12][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 543883822-Methoxymethoxy-5-(trifluoromethyl)benzyl alcohol

Product 1

HCID 233631292-(Hydroxymethyl)-4-(trifluoromethyl)phenolYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 2-methoxymethoxy-5-(trifluoromethyl)benzyl alcohol (3.15 g) from Example 60 in methanol (20 ml) was added 10% H2SO4 (5 ml) for reflux under heating for 1 hour. The solvent was removed under reduced pressure. To the residue was added water, the aqueous layer was extracted with ether. The ether layer was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, to give the title compound (2.5 g; 98%).

Workup

  1. temperaturefor reflux
  2. temperatureunder heating for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe aqueous layer was extracted with ether
  6. washThe ether layer was washed with water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d66bc06660dd4cf3b374e6e6b8b1da33
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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