Acetic Acid → HCID 20323915, compound

HRID 441792Notes

Reaction equation

HRID 441792 reaction equation
[Na].[OH:2][CH:3]([C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=1)=[CH2:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)(=O)C>C(O)C>[CH3:10][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=1)[C:3](=[O:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 21417892HCID 21417892, compound

Product 1

HCID 20323915HCID 20323915, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 0.5 g of metallic sodium in 50 ml of anhydrous ethanol was added a solution of 3.0 g of ethyl 2-hydroxy-3-(3-benzoylphenyl)-3-butenoate in 20 ml of anhydrous ethanol. The resulting mixture was refluxed for 20 minutes and then cooled. The reaction liquid was charged with 5 ml of glacial acetic acid, and the ethanol was removed therefrom by distillation at a low temperature and under reduced pressure. The residue was charged with ethyl acetate and water, thereby effecting ethyl acetate extraction. The ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water, and then dried over anhydrous magnesium sulfate. Thereafter, the ethyl acetate was removed by distillation under reduced pressure to obtain 2.2 g of ethyl 3-methyl-3-(3-benzoylphenyl)-pyruvate. The yield was 73%.

Workup

  1. temperatureThe resulting mixture was refluxed for 20 minutes
  2. temperaturecooled
  3. customThe reaction liquid
  4. customthe ethanol was removed
  5. distillationby distillation at a low temperature
  6. additionThe residue was charged with ethyl acetate and water
  7. extractioneffecting ethyl acetate extraction
  8. washThe ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThereafter, the ethyl acetate was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5a8cdefff7c243b69060f73790bcdeee
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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