Water → 3'-Chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxylic acid

HRID 1370027Notes

Reaction equation

HRID 1370027 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]([Cl:19])[CH:10]=1)#N.[OH-:20].[K+].[OH2:22]>>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([C:4]2[C:3]([C:1]([OH:22])=[O:20])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:10][C:11]=1[Cl:19]

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 185171353'-Chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-2-carbonitrile

Product 1

HCID 185171383'-Chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-2-carboxylic acid

Conditions

Temperature
160 °C

Procedure

60 g of 2-cyano-3′-chloro-4′-trifluoromethylbiphenyl were mixed with a solution of 38.7 g of potassium hydroxide in 325 ml of water and stirred at 160° C. under autogenous pressure in an autoclave for 24 hours. The autoclave was then cooled and the aqueous reaction mixture was filtered through Celite and subsequently extracted twice with 200 ml of toluene each time. The aqueous phase was brought to a pH of 6 to 7 with 10% strength hydrochloric acid. The precipitated solid was filtered off, washed with water, and dried. 30 g (47% of theory) of a bale beige solid of melting point 181 to 184° C. were obtained in a purity of 92.7% (HPLC, area percent).

Workup

  1. temperatureThe autoclave was then cooled
  2. filtrationthe aqueous reaction mixture was filtered through Celite
  3. extractionsubsequently extracted twice with 200 ml of toluene each time
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water
  6. customdried
  7. custom30 g (47% of theory) of a bale beige solid of melting point 181 to 184° C. were obtained in a purity of 92.7% (HPLC, area percent)

Sources & evidence

ORD record
ord-5b27153068c84091866bbc3fc2d80a95
Source dataset
uspto-grants-2003_06
Patent number
US06580002B2

Reaction notes

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