Water → HCID 12223963, compound

HRID 435720Notes

Reaction equation

HRID 435720 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18][C:19]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:21].[Na+].[OH2:23]>C(O)C>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[CH2:18][C:19]([OH:23])=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 122239582-Phenylthio-5-trifluoromethyl-phenylacetonitrile

Product 1

HCID 12223963HCID 12223963, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 g of 2-phenylthio-5-trifluoromethyl-phenylacetonitrile, 15.1 g of sodium hydroxide, 90 ml of water and 23 ml of ethanol are heated under reflux for 12 hours and subsequently concentrated. After the addition of 200 ml of water, the residue is extracted with 100 ml of benzene. The aqueous phase is back-extracted with 50 ml of benzene. The combined organic phases are extracted with 0.5-N aqueous sodium hydroxide solution. The aqueous phase is acidified with hydrochloric acid and extracted with 150 ml of chloroform. The organic phase is washed with aqueous sodium chloride solution, dried and evaporated. There is obtained 2 -(phenylthio)-5-trifluoromethyl-phenylacetic acid in the form of crystals which melt at 102°-103° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. concentrationsubsequently concentrated
  3. additionAfter the addition of 200 ml of water
  4. extractionthe residue is extracted with 100 ml of benzene
  5. extractionThe aqueous phase is back-extracted with 50 ml of benzene
  6. extractionThe combined organic phases are extracted with 0.5-N aqueous sodium hydroxide solution
  7. extractionextracted with 150 ml of chloroform
  8. washThe organic phase is washed with aqueous sodium chloride solution
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-ae4b3bb6c9eb42198118ba4c69e02b07
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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