Ethanol → HCID 54538359, compound

HRID 1731178Notes

Reaction equation

HRID 1731178 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[K+]>O>[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 53820247Ethyl 4-(m-benzoylphenyl)-3-butenoate

Product 1

HCID 54538359HCID 54538359, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 275 mg of ethyl 4-(m-benzoyl-phenyl)-3-butenoate, 2.75 ml of ethanol, 0.275 ml of ethanol, 0.275 ml of water and 0.08 ml of 12.5N potassium hydroxide was refluxed for 30 minutes and then was evaporated to dryness. The residue was dissolved in 10 ml of water and the solution was treated with activated carbon, and filtered. 3 ml of N hydrochloric acid were added thereto and the mixture was extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure to obtain 166 mg of 4-(m-benzoyl-phenyl)-3-butenoic acid in the form of a yellow oil soluble in chloroform and ethanol and insoluble in water.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customwas evaporated to dryness
  3. dissolutionThe residue was dissolved in 10 ml of water
  4. additionthe solution was treated with activated carbon
  5. filtrationfiltered
  6. addition3 ml of N hydrochloric acid were added
  7. extractionthe mixture was extracted with methylene chloride
  8. washThe organic phase was washed with water
  9. dry with materialdried over sodium sulfate
  10. additiontreated with activated carbon
  11. filtrationfiltered
  12. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ede664cd509e4f3eb9d69638206814dd
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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