1-Chloro-4-(trifluoromethyl)benzene → 4-(Trifluoromethyl)benzoic acid

HRID 1613966Notes

Reaction equation

HRID 1613966 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12](=O)([O-:14])[O-:13].[Na+].[Na+].[C]=O>[C].[Pd].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:12]([OH:14])=[O:13])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 10340Sodium CarbonateHCID 178418416HCID 178418416, compound2×

Product 1

HCID 99664-(Trifluoromethyl)benzoic acidYield 265.6%

Reagents, catalysts & solvents 3

HCID 821241,4-Bis(diphenylphosphino)butaneCatalystHCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

In an autoclave made of glass were placed 180.6 g of parachlorobenzotrifluoride, 0.64 g of 5% palladium-carbon, 4.3 g of 1,4-bisdiphenylphosphinobutane and 21.2 g of sodium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto several times, after which carbon monoxide was further introduced to adjust its pressure therein to 10 kg/cm2. The reaction was carried out with stirring for 8 hours at 180° C. After completion of the reaction, the reaction mixture was cooled to room temperature and water was added. The aqueous layer was separated and then acid was added thereto, followed by extraction from the aqueous layer with ether. The ether layer was dried and then concentrated to obtain 101 g of paratrifluoromethylbenzoic acid.

Workup

  1. additionintroduced
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customThe aqueous layer was separated
  5. additionacid was added
  6. extractionfollowed by extraction from the aqueous layer with ether
  7. dry with materialThe ether layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7e26addbca144f9293f7dea343edc70d
Source dataset
uspto-grants-1993_03
Patent number
US05194631

Reaction notes

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