Acetic Acid → HCID 12264291, compound

HRID 441787Notes

Reaction equation

HRID 441787 reaction equation
[Na].[OH:2][CH:3]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[CH2:9])[C:4]([O:6][CH3:7])=[O:5].C(O)(=O)C>CO>[CH3:9][CH:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)[C:3](=[O:2])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 12264285HCID 12264285, compound

Product 1

HCID 12264291HCID 12264291, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 0.3 g of metallic sodium in 30 ml of anhydrous methanol was added a solution of 3.1 g of methyl 2-hydroxy-3-(4-biphenylyl)-3-butenoate in 10 ml of anhydrous methanol. The resulting mixture was refluxed for 30 minutes and then cooled, and thereto was added 3 ml of glacial acetic acid. The mixture was distilled at a low temperature and under reduced pressure to remove the methanol therefrom. To the residue were added 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 dried over anhydrous magnesium sulfate. The ethyl acetate was removed by distillation under reduced pressure to obtain crude crystals. 3.0 Grams of the crude crystals was recrystallized from isopropyl alcohol to obtain 1.9 g of methyl 3-methyl-3-(4-biphenylyl)-pyruvate, m.p. 84.5°-86.5° C. The yield was 61% (theoretical value).

Workup

  1. temperatureThe resulting mixture was refluxed for 30 minutes
  2. temperaturecooled
  3. distillationThe mixture was distilled at a low temperature and under reduced pressure
  4. customto remove the methanol
  5. additionTo the residue were added ethyl acetate and water
  6. extractioneffecting ethyl acetate extraction
  7. washThe ethyl acetate layer was successively washed with water, aqueous sodium bicarbonate solution and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe ethyl acetate was removed by distillation under reduced pressure
  10. customto obtain crude crystals
  11. custom3.0 Grams of the crude crystals was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5ba6bdb9b5af441d9787673c88617d93
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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