Hydrochloric Acid → 2-Benzoylsulfanylbenzoic acid

HRID 2116792Notes

Reaction equation

HRID 2116792 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([O-])(O)=O.[Na+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O>[C:16]([S:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic Acid2×HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 2595062-Benzoylsulfanylbenzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Mercapto-benzoic acid (1.5 g, 9.73 mmol) was dissolved in a solution of NaHCO3 (2.6 g, 0.031 mol) in H2O (25 mL). The 2-mercapto-benzoic acid solution was cooled to 0° C. Benzoyl chloride (1.36 g, 9.73 mmol) was then added followed by additional Na2CO3 (2.01 g, 14.60 mmol). The reaction mixture was stirred for 30 min at 0° C. and then, after allowing it to warm to room temperature, the reaction mixture was allowed to stir for an additional 45 minutes. Subsequently the reaction mixture was acidified with concentrated HCl forming a white precipitate. The precipitate was collected washed with cold water and dried in a vacuum dessicator overnight to yield the title compound in 83% yield (2.08 g, 8.08 mmol).

Workup

  1. temperatureto warm to room temperature
  2. stirringto stir for an additional 45 minutes
  3. customThe precipitate was collected
  4. washwashed with cold water
  5. customdried in a vacuum dessicator overnight

Sources & evidence

ORD record
ord-0d1ac09c6ae84f0bb8769bb6c1b63a79
Source dataset
uspto-grants-2008_10
Patent number
US07439371B2

Reaction notes

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