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

HRID 435609Notes

Reaction equation

HRID 435609 reaction equation
[CH3:1][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>[CH3:1][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 125391013-Methyl-6-(phenylthio)-phenylacetonitrile

Product 1

HCID 125391053-Methyl-6-(phenylthio)-phenylacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

500 g of 3-methyl-6-(phenylthio)-phenylacetonitrile, 1.2 litres of ethanol, 470 g of potassium hydroxide and 500 ml of water are heated for 12 hours under reflux. Then the ethanol is evaporated off under reduced pressure. The residue is treated with water until completely dissolved and the neutral constituents are extracted with benzene. The aqueous solution is filtered with the addition of some dicalite and active carbon, cooled and adjusted to pH 3 with concentrated hydrochloric acid. The mixture is then extracted three times with 1 litre of chloroform each time and the extracts are washed with water, dried over calcium chloride, filtered and concentrated under reduced pressure. The crude 3-methyl-6-(phenylthio)-phenylacetic acid obtained is recrystallised from benzene/hexane; melting point 132°-135° C.

Workup

  1. temperatureunder reflux
  2. customThen the ethanol is evaporated off under reduced pressure
  3. additionThe residue is treated with water
  4. dissolutionuntil completely dissolved
  5. extractionthe neutral constituents are extracted with benzene
  6. filtrationThe aqueous solution is filtered with the addition of some dicalite and active carbon
  7. temperaturecooled
  8. extractionThe mixture is then extracted three times with 1 litre of chloroform each time
  9. washthe extracts are washed with water
  10. dry with materialdried over calcium chloride
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c28e7ea782a94a0f97cb869f3c4acad3
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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