Carbon Dioxide → 5-Trifluoromethoxysalicylic acid

HRID 1031885

Reaction equation

HRID 1031885 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[C:13](=O)([O-:15])[O-:14].[K+].[K+].C(=O)=O>O>[OH:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][C:8]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 27751035-Trifluoromethoxysalicylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

178 g (1 mol) of 4-trifluoromethoxyphenol and 345 g (2.5 mol) of potassium carbonate were initially introduced into an autoclave which was then pressurized to 60 bar with carbon dioxide and heated at 200° C. for 4 hours. After cooling and releasing the pressure, the residue was dissolved in 1.5 l of hot water, the solution was filtered hot, the cooled filtrate was extracted using methylene chloride and the extract was clarified using active carbon. The pH was then adjusted to 1 and the precipitated product was filtered off with suction. 192 g of product having a melting point of 129° C. were obtained, which corresponds to 86% of theory.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solution was filtered hot
  3. extractionthe cooled filtrate was extracted
  4. filtrationthe precipitated product was filtered off with suction
  5. customwere obtained

Sources & evidence

ORD record
ord-753b479947974eae883af69265b3ba90
Source dataset
uspto-grants-1990_09
Patent number
US04956370

Linked notes

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