Water → {2-[(4-Chloro-3-methoxyphenyl)sulfanyl]phenyl}acetic acid

HRID 1732772Notes

Reaction equation

HRID 1732772 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]#N)=[CH:6][C:5]=1[O:20][CH3:21].[OH2:22]>C(O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([OH:22])=[O:1])=[CH:6][C:5]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 12374611{2-[(4-Chloro-3-methoxyphenyl)sulfanyl]phenyl}acetonitrile

Product 1

HCID 12374613{2-[(4-Chloro-3-methoxyphenyl)sulfanyl]phenyl}acetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of potassium hydroxide (8.25 g) in water (20 ml) is added to a solution of the above-prepared nitrile (8.8 g) in ethanol (30 ml) and the mixture refluxed for 4 hours. The ethanol is evaporated under diminished pressure and the residue diluted with water. The solution is washed with ether, cooled and acidified with hydrochloric acid. The crude product is filtered and crystallized from a mixture of benzene (10 ml) and light petroleum (25 ml), yielding 8.5 g (90%) of 2-(4-chloro-3-methoxyphenylthio)phenylacetic acid. The pure product melts at 103°-105° C.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. customThe ethanol is evaporated under diminished pressure
  3. additionthe residue diluted with water
  4. washThe solution is washed with ether
  5. temperaturecooled
  6. filtrationThe crude product is filtered
  7. customcrystallized from a mixture of benzene (10 ml) and light petroleum (25 ml)

Sources & evidence

ORD record
ord-f2368481ce86460a80f42e56945b21cd
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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