Ethanol → 2-Methylsulphonyl-3-phenylsulphenylbenzoic acid

HRID 1491579Notes

Reaction equation

HRID 1491579 reaction equation
[CH3:1][S:2]([C:5]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])(=[O:4])=[O:3].C(O)C.[OH-].[Na+]>O>[CH3:1][S:2]([C:5]1[C:14]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18953302Methyl 2-methylsulphonyl-3-phenylsulphenylbenzoate

Product 1

HCID 189533112-Methylsulphonyl-3-phenylsulphenylbenzoic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2 -methylsulphonyl-3-phenylsulphenylbenzoate (8.3 g), ethanol (50 ml) and 2N sodium hydroxide (25 ml) was heated at reflux for one hour and then added to water. The inorganic phase was washed with ethyl acetate, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. This organic phase was dried over sodium sulphate, filtered and evaporated giving 7.9 g of 2-methylsulphonyl-3-phenylsulphenylbenzoic acid as a white solid, m.p. 185.4°-186.0° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. washThe inorganic phase was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThis organic phase was dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2bea5c5b7e5f4d37890d6d902c04f47e
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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