Hydrochloric Acid → 2-Chloro-5-(methylsulphonyl)benzoic acid

HRID 2174679Notes

Reaction equation

HRID 2174679 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](SC)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13]([O-])(O)=O.[Na+].O[O:19][S:20]([O-:22])=O.[K+].[O-]S([O-])(=S)=O.[Na+].[Na+].Cl>[OH-].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:20]([CH3:13])(=[O:22])=[O:19])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 6049Ethylenediaminetetraacetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-chloro-5-(methylthio)benzoic acid (6.05 g, 30 mmol) and NaHCO3 (20 g, 240 mmol) in NaOH 0.5N (75 ml) a solution of oxone (24 g) in EDTA (0.0004M, 90 ml) was added. After 1 hour at RT Na2S2O3 (15 g in 100 ml of water) was added; after 10 min HCl 4N was added to pH 2. The white solid was filtered, washed with water and dried in vacuum at 70° C. Yield 6 g white solid.

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with water
  3. customdried in vacuum at 70° C

Sources & evidence

ORD record
ord-1af98a6918ec49cb861a10248b48a5e4
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Reaction notes

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