2-Mercaptobenzoic Acid → HCID 13770735, compound

HRID 255583Notes

Reaction equation

HRID 255583 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]([OH:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[SH:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>C(O)C1C=CC=CC=1.[Cu]>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]([OH:21])=[O:20])[CH:10]=1

Participants

7

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 57872,4-Dichlorobenzoic AcidHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 13770735HCID 13770735, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 244Benzyl AlcoholSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2,4-dichlorobenzoic acid (7.64 g), thiosalicylic acid (7.16 g), anhydrous potassium carbonate (22 g), and copper powder (300 mg) was suspended in benzyl alcohol and this suspension was heated under N2 atmosphere at 110-120° C. for 3 hours. After cooling, 10% aqueous potassium hydroxide solution (120 ml) was added and extracted with ether. The aqueous layer was filtered and acidified with 6N HCl. The resulting precipitated product was isolated by filtration. Recrystallization from aqueous methanol gave 4-chloro-2,2'-thiodibenzoic acid (compound No. 1) in an amount of 8.56 g (yield: 70%). m.p. 241-242° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. filtrationThe aqueous layer was filtered
  4. customThe resulting precipitated product
  5. customwas isolated by filtration
  6. customRecrystallization from aqueous methanol

Sources & evidence

ORD record
ord-ab789ed842ae43239327f690efcd1f31
Source dataset
uspto-grants-1987_10
Patent number
US04698364

Reaction notes

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