Hydrochloric Acid → 5-Methyl-2-(phenylsulfanyl)benzoic acid

HRID 435662Notes

Reaction equation

HRID 435662 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[C:11]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].Cl>O.[Cu]>[CH3:20][C:17]1[CH:16]=[C:12]([C:11]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 1429412-Iodo-5-methylbenzoic acid

Product 1

HCID 125390985-Methyl-2-(phenylsulfanyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a solution of 855 g of potassium hydroxide in 7 litres of water are added, at 50° C under argon, 420 g of thiophenol and the mixture is stirred for 15 minutes. There are then added thereto 22.1 g of copper powder and 1 kg of 2-iodo-5-methyl-benzoic acid and the mixture is heated for 7 hours under reflux. After cooling, the mixture is adjusted to pH 3 with 600 ml of concentrated hydrochloric acid and extracted with methylene chloride, washed with water, dried over sodium sulphate and concentrated to a thick crystal mash. This is filtered under suction, washed with cold ethanol and low-boiling petroleum ether and dried. There is obtained 3-methyl-6-(phenylthio)-benzoic acid of melting point 156°-157° C.

Workup

  1. additionThere are then added
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. extractionextracted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to a thick crystal mash
  8. filtrationThis is filtered under suction
  9. washwashed with cold ethanol and low-boiling petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-f54f07ba2f244678b7a4eb019d63f6a1
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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