Methanesulfonic Acid → HCID 14054310, compound

HRID 1382854Notes

Reaction equation

HRID 1382854 reaction equation
[C:1]1([C:7]2[O:11][C:10](=[O:12])[C:9](=[CH:13][C:14]3[CH:18]=[CH:17][S:16][CH:15]=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:15]3[S:16][CH:17]=[CH:18][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 888118HCID 888118, compound

Product 1

HCID 14054310HCID 14054310, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

5-Phenyl-3-(3-thienylmethylene)-2-furanone (44.7 g), methanesulfonic acid (220 cc) and glacial acetic acid (220 cc) are heated for 1 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 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 off and the organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The evaporation residue and the precipitate are combined and stirred in ethyl acetate in the presence of silica gel (100 g). The silica is removed by filtration and the ethyl acetate evaporated under reduced pressure. This operation is repeated to produce 7-phenylbenzo[b]thiophene-5-carboxylic acid (29 g), m.p. 234° C.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionextracted with methylene chloride
  4. washThe organic phase is washed with water
  5. extractionextracted with 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 off
  11. dry with materialthe organic phase is dried over magnesium sulfate
  12. customevaporated under reduced pressure
  13. customThe silica is removed by filtration
  14. customthe ethyl acetate evaporated under reduced pressure

Sources & evidence

ORD record
ord-a24c785550c64647b6482444ed41f08f
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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