Ethanol → 2-Methyl-3-(2-thenoyl)hydratropic acid

HRID 258928Notes

Reaction equation

HRID 258928 reaction equation
[CH3:1][C:2]1[C:11]([C:12](=[O:18])[C:13]2[S:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[CH:4]([CH3:7])[C:5]#N.[OH-:19].[K+].C([OH:23])C>O>[CH3:1][C:2]1[C:11]([C:12](=[O:18])[C:13]2[S:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][C:3]=1[CH:4]([CH3:7])[C:5]([OH:23])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 213917872-Methyl-3-(2-thenoyl)hydratroponitrile

Product 1

HCID 213917512-Methyl-3-(2-thenoyl)hydratropic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6 parts of 2-methyl-3-(2-thenoyl)hydratroponitrile, 2.7 parts of potassium hydroxide, 28 parts of ethanol and 3.5 parts of water is stirred and refluxed for 44 hours. The reaction mixture is evaporated. The residue is taken up in water and washed twice with 80 parts of ether. The aqueous phase is acidified with concentrated hydrochloric acid solution. The separated oily product is extracted with ether. Then the latter is dried and evaporated. The oily residue solidifies on triturating in petroleumether. The product is crystallized from acetonitrile -20° C, yielding a first fraction of 2-methyl-3-(2-thenoyl)hydratropic acid; mp. 118.7° C.

Workup

  1. temperaturerefluxed for 44 hours
  2. customThe reaction mixture is evaporated
  3. washwashed twice with 80 parts of ether
  4. extractionThe separated oily product is extracted with ether
  5. customThen the latter is dried
  6. customevaporated
  7. customon triturating in petroleumether
  8. customThe product is crystallized from acetonitrile -20° C

Sources & evidence

ORD record
ord-b7423183456a497fb9df6ab9089836fa
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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