Water → 4-Benzenesulfinyl-benzoic acid

HRID 1177870Notes

Reaction equation

HRID 1177870 reaction equation
S(=O)(=O)(O)N.[C:6]1([S:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl([O-])=[O:22].[Na+].[OH2:25]>CC(C)=O>[C:6]1([S:12]([C:13]2[CH:20]=[CH:19][C:16]([C:17]([OH:22])=[O:18])=[CH:15][CH:14]=2)=[O:25])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 5987Sulfamic AcidHCID 71023Benzaldehyde, p-phenylthio-HCID 23668197Sodium Chlorite2×

Product 1

HCID 3438114-Benzenesulfinyl-benzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Sulphamic acid (0.272 g, 2.80 mmol) in 2 mL water was added to 4-phenylsulfanyl-benzaldehyde (0.2 g, 0.93 mmol) in 5 mL acetone at 0° C. After 5 minutes, sodium chlorite (0.338 g, 3.74 mmol) was added and the mixture stirred at 0° C. for 30 minutes. Sodium chlorite (0.676 g, 7.48 mmol) was then added and the resulting mixture was stirred at room temperature overnight. Water was then added and the resulting solid was filtered to afford 140 mg (60% yield) of 4-benzenesulfinyl-benzoic acid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-c77eef345b4647588187e1c4416606c4
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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