Hydrochloric Acid → 3-Chloro-4-hydroxy-2-(trifluoromethyl)benzaldehyde

HRID 1815512Notes

Reaction equation

HRID 1815512 reaction equation
C(Cl)(Cl)Cl.[C:5]([O-])([O-])=[O:6].[K+].[K+].[Cl:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:13]=1[OH:22].Cl>O>[Cl:11][C:12]1[C:17]([C:18]([F:20])([F:21])[F:19])=[C:16]([CH:15]=[CH:14][C:13]=1[OH:22])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 11430Potassium CarbonateHCID 27366012-Chloro-3-(trifluoromethyl)phenol

Product 1

HCID 109331373-Chloro-4-hydroxy-2-(trifluoromethyl)benzaldehydeYield 11.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloroform (6.7 g, 2.0 eq.) was added dropwise to a stirred mixture of Ca(OH)2 (8.95 g, 120 mmol.), K2CO3 (13.5 g, 98 mmol.), 2-chloro-3-(trifluoromethyl)phenol (50. g, 22 mmol.), and H2O (50 mL) at 60°-70° over 2 hours. The reaction mixture was cooled, and acidified with conc. HCl. The product was extracted into EtOAc and dried over Na2SO4. Solvent was evaporated, the crude product was separated and purified through a silica column, eluting with hexane and EtOAc (3:2) to give 580 mg (10%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted into EtOAc
  3. dry with materialdried over Na2SO4
  4. customSolvent was evaporated
  5. customthe crude product was separated
  6. custompurified through a silica column
  7. washeluting with hexane and EtOAc (3:2)

Sources & evidence

ORD record
ord-5e3af036466b4b18a8b50dc0626ad529
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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