Acetone → 2-Hydroxyisobutyric acid

HRID 1196115Notes

Reaction equation

HRID 1196115 reaction equation
[OH-:1].[Na+].CC(C)=[O:5].[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][OH:24])=[N:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)(Cl)Cl.[OH2:29]>>[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][OH:24])=[N:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[OH:1][C:17]([CH3:16])([CH3:22])[C:18]([OH:5])=[O:29]

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 10657568(1-Benzylindazol-3-yl)methanol

Product 2

HCID 116712-Hydroxyisobutyric acidHCID 10657568(1-Benzylindazol-3-yl)methanol

Procedure

Into a round-bottomed flask, provided with a vigorous stirrer, 1.9 g of NaOH, 10 g of acetone and 2.38 g of 1-benzyl-3-hydroxymethyl-indazole, prepared as described above, are successively added. 1.6 g of chloroform are then added (exothermic reaction) and the mixture is heated for two hours on a water bath. Water is added, the reaction mixture is washed with ethyl acetate and the aqueous solution is acidified. The residue is recrystallized from a mixture of hexane/ethyl acetate 1:1. The ether of 1-benzyl-3-hydroxymethyl-indazole with 2-hydroxy-2-methyl-propionic acid is thus obtained (Compound I, R=R'=CH3, R'"=H), m.p. 132°-134° C.

Workup

  1. customInto a round-bottomed flask, provided with a vigorous stirrer
  2. additionare successively added
  3. custom(exothermic reaction)
  4. temperaturethe mixture is heated for two hours on a water bath
  5. washthe reaction mixture is washed with ethyl acetate
  6. customThe residue is recrystallized from a mixture of hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-2b814965088a480a83efb489b08ba4c3
Source dataset
uspto-grants-1992_05
Patent number
US05112986

Reaction notes

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