Citric Acid → 4-Hydroxy-3-(trifluoromethyl)benzoic acid

HRID 2116693Notes

Reaction equation

HRID 2116693 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].Cl.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 3

HCID 311Citric AcidHCID 27752954-Methoxy-3-(trifluoromethyl)benzoic acidHCID 10176127Pyridinium chloride

Product 1

HCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Conditions

Temperature
180 °C

Procedure

A mixture of 10.0 g (45.4 mmol) 4-methoxy-3-trifluoromethyl-benzoic acid and 75 g (649 mmol) pyridine hydrochloride was stirred for 5 hours at 180° C. under nitrogen gas. The reaction mixture was then poured onto 1 L of 10% citric acid solution, extracted with 500 ml EtOAc, the organic phase washed with 1 L water, dried and evaporated down under reduced pressure.

Workup

  1. extractionextracted with 500 ml EtOAc
  2. washthe organic phase washed with 1 L water
  3. customdried
  4. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-3512ab8e86cc476fbac4753dc66d7e73
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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