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

HRID 991970Notes

Reaction equation

HRID 991970 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 per cent).

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 per cent)

Sources & evidence

ORD record
ord-5984e29ce5a74ea7aa5058319ca28e73
Source dataset
uspto-grants-2002_10
Patent number
US06465688B2

Reaction notes

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