Sulfuric Acid → 3-[(Phenylmethyl)sulfonyl]-5-(trifluoromethyl)benzoic acid

HRID 1076145Notes

Reaction equation

HRID 1076145 reaction equation
[CH2:1]([S:8]([C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:14]([O:16]CC1C=CC=CC=1)=[O:15])(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH2:1]([S:8]([C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[C:14]([OH:16])=[O:15])(=[O:10])=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21542495HCID 21542495, compound

Product 1

HCID 215421333-[(Phenylmethyl)sulfonyl]-5-(trifluoromethyl)benzoic acid

Procedure

0.10 moles of benzyl 3-benzylsulfonyl-5-trifluoromethylbenzoate is refluxed in a 10 percent sulfuric acid solution for 1 hour. The reaction mixture is cooled, made alkaline with sodium hydroxide and extracted with ether. The aqueous phase is acidified and extracted with ether. The ether extracts are dried over sodium sulfate and evaporated to give 3-benzylsulfonyl-5-trifluoromethylbenzoic acid, m.p. 184°-185.5°C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ether
  3. extractionextracted with ether
  4. dry with materialThe ether extracts are dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-cb21f613eab94f999a8ce672434d195f
Source dataset
uspto-grants-1976_05
Patent number
US03954994

Reaction notes

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