Hydrochloric Acid → 2-Hydroxy-4-(trifluoromethyl)benzaldehyde

HRID 2259611Notes

Reaction equation

HRID 2259611 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[Cl-].[Li+].CN(C)C=O.Cl>O>[OH:2][C:3]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 224939012-Hydroxy-4-(trifluoromethyl)benzaldehydeYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 10.0 g (0.042 mol) 2-methoxy-4-(trifluoromethyl)benzaldehyde, 5.3 g (0.126 mol) lithium chloride, and 50 mL of dimethylformamide was heated at 155° C. for 3 hours. The reaction mass was cooled, diluted with 100 mL of water, acidified with hydrochloric acid, and then extracted three times with 100 mL of ether. The ether extracts were washed with water, dried over anhydrous magnesium sulfate, and evaporated to provide 6.8 g of the product as an oil.

Workup

  1. temperatureThe reaction mass was cooled
  2. extractionextracted three times with 100 mL of ether
  3. washThe ether extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4ae09f1a0652445e963dbc6de6cef5a8
Source dataset
uspto-grants-1995_12
Patent number
US05474998

Reaction notes

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