2-Mercaptobenzoic Acid → 2-Styrylsulfanylbenzoic acid

HRID 48323

Reaction equation

HRID 48323 reaction equation
C(Br)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([OH:20])(=[O:19])[C:12]1[C:13](=[CH:15][CH:16]=[CH:17][CH:18]=1)[SH:14]>C(O)C.[OH-].[Na+]>[CH:2]([S:14][C:13]1[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=1[C:11]([OH:20])=[O:19])=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 54432-Mercaptobenzoic AcidHCID 98116Bromomethylstyrene

Product 1

HCID 698934372-Styrylsulfanylbenzoic acidYield 102.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1.28 g (6.49 mmol) of cinnamyl bromide in 8 ml of ethanol at room temperature under an atmosphere of nitrogen was added a solution of 1 g (6.49 mmol) of thiosalicylic acid in 5.3 ml of 10% aqueous sodium hydroxide solution. The solution was stirred at room temperature for 16 hours and the solvent then removed under reduced pressure. The residue was dissolved in water and concentrated hydrochloric acid was added. The resultant solid was filtered off and dried. There was obtained 1.7 g of 2-styrylsulfanylbenzoic acid as a white solid, MS: m/e 270 M+.

Workup

  1. customthe solvent then removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionconcentrated hydrochloric acid was added
  4. filtrationThe resultant solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-7a3900057be74659a2b64eb7fa456122
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Linked notes

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