Chlorobenzene → Benzoic Acid

HRID 1613962

Reaction equation

HRID 1613962 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C(C(P(C2C=CC=CC=2)C2C=CC=CC=2)C)C)C2C=CC=CC=2)C=CC=CC=1.[C:38](=O)([O-:40])[O-:39].[K+].[K+].[C]=O>[Pd](Cl)Cl.O>[C:38]([OH:40])(=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7964ChlorobenzeneHCID 11430Potassium CarbonateHCID 3882352ChiraphosHCID 178418416HCID 178418416, compound2×

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

In an autoclave made of metal were placed 11.2 g of chlorobenzene, 17.5 mg of palladium chloride, 427 mg of bisdiphenylphosphinobutane and 3.1 g of potassium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto in several times, after which carbon monoxide was further introduced to its pressure therein to 50 kg/cm2. The reaction was carried out with stirring for 3 hours on a salt bath at a bath temperature of 210° C. After completion of the reaction, the reaction mixture was cooled to room temperature and water was added. The aqueous layer was separated, after which acid was added thereto and the deposited crystals were collected by

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. additionafter which acid was added
  6. customthe deposited crystals were collected by

Sources & evidence

ORD record
ord-095b683e6d924901b542fa981debd102
Source dataset
uspto-grants-1993_03
Patent number
US05194631

Linked notes

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