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

HRID 1181426Notes

Reaction equation

HRID 1181426 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+].O.Cl>CN(C)C=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 962WaterHCID 433294Lithium ChlorideHCID 49847042-Methoxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 224939012-Hydroxy-4-(trifluoromethyl)benzaldehydeYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxy-4-trifluoromethyl benzaldehyde (Description 96; 18 g, 88 mmol) and lithium chloride (11.19 g; 264 mmol) in anhydrous N,N-dimethylformamide (100 ml) was heated at reflux for 3 hours. The mixture was cooled and poured into water (200 ml), then acidified by the addition of 1N HCl. The mixture was extracted with ether (3×200 ml) then the combined ether layers washed with water (2×500 ml), sat NaCl (100 ml), dried over Na2SO4, filtered and evaporated to give the title compound (16.25 g, 97%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. extractionThe mixture was extracted with ether (3×200 ml)
  5. washthe combined ether layers washed with water (2×500 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c429a7dadfed4a978a2543a9165d3b6f
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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