Potassium Hydroxide → 4-Methoxy-6-[(4-methylthio-phenyl)-thio]-benzoic acid

HRID 1973090Notes

Reaction equation

HRID 1973090 reaction equation
[OH-].[K+].[CH3:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.I[C:13]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]>O.[Cu]>[CH3:23][O:22][C:20]1[CH:21]=[C:13]([S:11][C:8]2[CH:9]=[CH:10][C:5]([S:4][CH3:3])=[CH:6][CH:7]=2)[C:14]([C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1368964-(Methylsulfanyl)thiophenolHCID 128221822-Iodo-4-methoxybenzoic acid

Product 1

HCID 128221844-Methoxy-6-[(4-methylthio-phenyl)-thio]-benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A solution of 170 g. of potassium hydroxide in 1.6 liters of water is treated under a nitrogen atmosphere at 50° C. with 102 g. of 4-methylthio-thiophenol. The resulting mixture is stirred for an additional 15 minutes. The mixture is then treated with 2.4 g. of copper powder and 180 g. of 2-iodo-4-methoxy-benzoic acid and heated under reflux for 7 hours. The mixture is filtered while hot, acidified with concentrated hydrochloric acid, cooled and filtered. The residue is washed with water, dried under reduced pressure, and there is obtained 4-methoxy-6-[(4-methylthio-phenyl)-thio]-benzoic acid having a melting point of 202°-203° C.

Workup

  1. additionThe mixture is then treated with 2.4 g
  2. temperatureunder reflux for 7 hours
  3. filtrationThe mixture is filtered while hot,
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe residue is washed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c10e44f882c54ef49e9cfe30f6456c88
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

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