Water → HCID 12264296, compound

HRID 441789Notes

Reaction equation

HRID 441789 reaction equation
[OH:1][CH:2]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)=[CH2:10])[C:3]([O:5]C(C)C)=[O:4].[K].O>C(O)(C)C>[CH3:10][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:15][CH:16]=1)[C:2](=[O:1])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 5462222PotassiumHCID 20323916HCID 20323916, compound

Product 1

HCID 12264296HCID 12264296, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

3.0 Grams of isopropyl 2-hydroxy-3-(4-cyclohexylphenyl)-3-butenoate was dissolved in 50 ml of anhydrous isopropyl alcohol. Separately, 1.1 g of metalic potassium was dissolved in 100 ml of anhydrous isopropyl alcohol. The two solutions thus prepared were combined together, and the combined solution was refluxed for 20 minutes. To the solution was then added 2 ml of water, and the mixture was further refluxed for 5 minutes. Thereafter, the isopropyl alcohol was removed from the mixture by distillation under reduced pressure. The residue was charged with water, and insoluble matter was removed therefrom by extraction with ethyl acetate. The extraction mother liquor was acidified with hydrochloric acid and then extracted with ethyl acetate. The ethyl acetate layer was successively washed with water and saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The ethyl acetate was removed by distillation under reduced pressure to obtain crude crystals. The crude crystals were recrystallized from benzene-hexane to obtain 2.15 g of 3-methyl-3-(4-cyclohexylphenyl)-pyruvic acid, m.p. 100.6°-102.5° C. The yield was 83%.

Workup

  1. customThe two solutions thus prepared
  2. temperaturethe combined solution was refluxed for 20 minutes
  3. temperaturethe mixture was further refluxed for 5 minutes
  4. customThereafter, the isopropyl alcohol was removed from the mixture by distillation under reduced pressure
  5. additionThe residue was charged with water, and insoluble matter
  6. customwas removed
  7. extractionby extraction with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was successively washed with water and saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe ethyl acetate was removed by distillation under reduced pressure
  12. customto obtain crude crystals
  13. customThe crude crystals were recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-5696cd42533146edb6f627e00cb9a8e3
Source dataset
uspto-grants-1977_08
Patent number
US04042617

Reaction notes

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