Methanesulfonic Acid → HCID 13637980, compound

HRID 1382857Notes

Reaction equation

HRID 1382857 reaction equation
[C:1]1([C:7]2[O:11][C:10](=[O:12])[C:9](=[CH:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(O)(=O)=O>C(O)(=O)C>[C:1]1([C:7]2[C:18]3[CH:17]=[CH:16][S:15][C:14]=3[CH:13]=[C:9]([C:10]([OH:11])=[O:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 785281HCID 785281, compound

Product 1

HCID 13637980HCID 13637980, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

5-Phenyl-3-(2-thienylmethylene)-2-furanone (34.9 g), methanesulfonic acid (170 cc) and glacial acetic acid (170 cc) are heated for one hour at 120° C. The mixture is cooled to 40° C., poured onto crushed ice and extracted with methylene chloride. The organic phase is washed with water and extracted with a normal sodium hydroxide solution. The basic aqueous phase is washed with methylene chloride, acidified to pH 1 by adding an aqueous hydrochloric acid solution and extracted with methylene chloride. The precipitate formed is filtered, the organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The evaporation residue and the precipitate are combined and chromatographed on silica gel using ethyl acetate as the eluent. 4-Phenylbenzo[b]thiophene-6-carboxylic acid (17.4 g), m.p. 222° C., is thereby isolated.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed with water
  5. extractionextracted with a normal sodium hydroxide solution
  6. washThe basic aqueous phase is washed with methylene chloride
  7. additionby adding an aqueous hydrochloric acid solution
  8. extractionextracted with methylene chloride
  9. customThe precipitate formed
  10. filtrationis filtered
  11. dry with materialthe organic phase is dried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. customchromatographed on silica gel

Sources & evidence

ORD record
ord-a548e949fd73416d9bfc27bd98ec6fd6
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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