2-Mercaptobenzoic Acid → 2-[(4-Carboxyphenyl)thio]benzoic acid

HRID 2373118Notes

Reaction equation

HRID 2373118 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([OH:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[SH:14]>[Cu].[Zn].[OH-].[Na+]>[S:14]([C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[C:11]([OH:20])=[O:19])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 54432-Mercaptobenzoic AcidHCID 120854-Iodobenzoic acid

Product 1

HCID 8267642-[(4-Carboxyphenyl)thio]benzoic acid

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 23994ZincCatalystHCID 14798Sodium HydroxideSolvent

Procedure

First, 2,4′-thiobis(benzoic acid) was prepared. A mixture of 4-iodobenzoic acid (55.7 g, 225 mmol), thiosalicylic acid (34.6 g, 225 mmol), copper powder (15 g, 236 mmol), zinc powder (3 g, 46 mmol), and 2.5 M aqueous sodium hydroxide (400 mL) was heated at reflux for 5 h and then cooled to ambient. The reaction mixture was filtered, and the filtrate was acidified with concentrated HCl. The precipitate was collected and washed with water, then dissolved and filtered. The filtrate was concentrated to deposit 2,4′-thiobis(benzoic acid), mass 50 g (81% of theory).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. temperaturecooled
  4. filtrationThe reaction mixture was filtered
  5. customThe precipitate was collected
  6. washwashed with water
  7. dissolutiondissolved
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e4077168dc75468aa1950b9c830a5b79
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

Loading…