2-Iodobenzoic acid → 2-[(2-Methoxyphenyl)sulfanyl]benzoic acid

HRID 977904Notes

Reaction equation

HRID 977904 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].I[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].[OH-].[K+]>[Cu].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 14797Potassium HydroxideHCID 23642Thioguaiacol

Product 1

HCID 155738872-[(2-Methoxyphenyl)sulfanyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

Stir under reflux for 3 hours a mixture of 70 gm (0.5 mole) of o-methoxythiophenol, 120.5 gm (0.486 mole) of o-iodobenzoic acid, 81.7 gm (1.46 mole) of potassium hydroxide, 85 gm (1.34 mole) of copper powder and 800 cc of water. Filter the reaction mixture hot and again filter the filtrate through celite. Acidify the filtrate with concentrated hydrochloric acid. Separate the precipitate, wash well with water and dry in vacuo at 70° C. to obtain the title product. (m.p. 198°-200° C.).

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationFilter the reaction mixture hot
  3. filtrationagain filter the filtrate through celite
  4. customSeparate the precipitate
  5. washwash well with water
  6. customdry in vacuo at 70° C.

Sources & evidence

ORD record
ord-a5a38ad45eb045e0a644d43a1ed27620
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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