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

HRID 1439580Notes

Reaction equation

HRID 1439580 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 at -20° C, yielding a first fraction of 2-methyl-3-(2-thenoyl)hydratropic acid; mp. 118.7° C. The mother-liquor is evaporated. The residue solidifies on triturating in petroleumether, yielding a second fraction of 2-methyl-3-(2-thenoyl)hydratropic acid; mp. 100° 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 at -20° C

Sources & evidence

ORD record
ord-dc59fe254380423492b32c71ada4df27
Source dataset
uspto-grants-1977_11
Patent number
US04060528

Reaction notes

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