Ethanol → 3-Fluoro-6-(phenylthio)-phenylacetic acid

HRID 435642Notes

Reaction equation

HRID 435642 reaction equation
[F:1][C:2]1[CH:3]=[C:4](CC#N)[C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1.[CH2:18]([OH:20])[CH3:19].[OH-:21].[K+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH2:19][C:18]([OH:21])=[O:20])[C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12232352HCID 12232352, compound

Product 1

HCID 122323553-Fluoro-6-(phenylthio)-phenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

80 g of 3-fluoro-6-(phenylthio)-phenylacetonitrile, 225 ml of ethanol, 75.5 g of potassium hydroxide and 225 ml of water are heated under reflux for 9 hours. The ethanol is subsequently evaporated off under reflux and the residue treated with water until completely dissolved, whereafter the neutral constituents are extracted with benzene. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with chloroform. The organic phase is washed with water, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 3-fluoro-6-(phenylthio)-phenylacetic acid which melts at 80°-83° C.

Workup

  1. temperatureunder reflux for 9 hours
  2. customThe ethanol is subsequently evaporated off
  3. temperatureunder reflux
  4. additionthe residue treated with water
  5. dissolutionuntil completely dissolved, whereafter the neutral constituents
  6. extractionare extracted with benzene
  7. extractionextracted with chloroform
  8. washThe organic phase is washed with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b5eeeaf06a90410db4d505734b30e98f
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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