Hydrochloric Acid → Ethyl p-(2-thenoyl)hydratropate

HRID 461700Notes

Reaction equation

HRID 461700 reaction equation
[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:20](O)[CH3:21]>>[C:1]1([C:6]([C:8]2[CH:18]=[CH:17][C:11]([CH:12]([CH3:16])[C:13]([O:15][CH2:20][CH3:21])=[O:14])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5359Suprofen

Product 1

HCID 12232951Ethyl p-(2-thenoyl)hydratropate

Procedure

A mixture of 5.2 parts of p-(2-thenoyl)hydratropic acid, 40 parts of absolute denatured ethanol and 0.5 parts of hydrochloric acid solution is stirred and refluxed for 24 hours. The reaction mixture is evaporated and the residue is taken up in ether. The ethereal solution is shaken with alkaline water, separated and shaken twice with water. The ether phase is dried, filtered and evaporated, yielding ethyl p-(2-thenoyl)hydratropate, also named ethyl p-(2-thenoyl)-α-methyl-phenylacetate, as a residue.

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe reaction mixture is evaporated
  3. stirringThe ethereal solution is shaken with alkaline water
  4. customseparated
  5. stirringshaken twice with water
  6. dry with materialThe ether phase is dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3ff24829aa724bcdaeb47e273cef728e
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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