Ethanol → HCID 53748896, compound

HRID 1731168Notes

Reaction equation

HRID 1731168 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH2:15][CH:16]=[C:17]([CH3:22])[C:18]([O:20]C)=[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]([CH2:15][CH:16]=[C:17]([CH3:22])[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 702EthanolHCID 14797Potassium HydroxideHCID 54140770HCID 54140770, compound

Product 1

HCID 53748896HCID 53748896, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 615 mg of methyl 4-(m-benzoyl-phenyl)-2-methyl-2-butenoate, 6.2 ml of ethanol, 0.6 ml of water and 0.4 ml of a concentrated aqueous solution of potassium hydroxide was refluxed for 1 hour and then was evaporated to dryness under reduced pressure. The residue was taken up in water and the solution was treated with activated carbon, filtered and acidified to a pH of 1 with 2 N hydrochloric acid. The solution was extracted with methylene chloride and the organic phase was washed with water, dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel with 90-10 ether-methylene chloride eluant to obtain 287 mg of 4-(m-benzoyl-phenyl)-2-methyl-2-butenoic acid in the form of an oil.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customwas evaporated to dryness under reduced pressure
  3. additionthe solution was treated with activated carbon
  4. filtrationfiltered
  5. extractionThe solution was extracted with methylene chloride
  6. washthe organic phase was washed with water
  7. dry with materialdried over sodium sulfate
  8. additiontreated with activated carbon
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe residue was chromatographed over silica gel with 90-10 ether-methylene chloride eluant

Sources & evidence

ORD record
ord-91809ddc554240929061be9ee79775a8
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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