Hydroxyamine hydrochloride → 2-(Hydroxyimino)-3,3-dimethylbutanoic acid

HRID 1298

Reaction equation

HRID 1298 reaction equation
[Na+].[CH3:2][C:3]([CH3:10])([CH3:9])[C:4](=O)[C:5]([O-:7])=[O:6].Cl.[NH2:12][OH:13]>O>[CH3:2][C:3]([CH3:10])([CH3:9])[C:4](=[N:12][OH:13])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23674764Sodium 3,3-dimethyl-2-oxobutyrate

Product 1

HCID 713816292-(Hydroxyimino)-3,3-dimethylbutanoic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

163 g (1 mole) 93.5% trimethylpyruvic acid sodium salt and 69.5 g (1 mole) hydroxylamine hydrochloride were dissolved at 40° C. in 450 ml water. The product crystallized out during slow cooling under agitation. After 1.5 h agitation in an ice bath the crystals were filtered off, washed with 150 ml ice water, dried in a vacuum at 60° C., and then further dried in a vacuum desiccator over phosphorus pentaoxide to constant weight. 117.8 g trimethylpyruvic acid oxime (81% yield) in the form of colorless crystals were obtained.

Workup

  1. customThe product crystallized out
  2. temperatureduring slow cooling under agitation
  3. filtrationAfter 1.5 h agitation in an ice bath the crystals were filtered off
  4. washwashed with 150 ml ice water
  5. customdried in a vacuum at 60° C.
  6. dry with materialfurther dried in a vacuum desiccator over phosphorus pentaoxide to constant weight

Sources & evidence

ORD record
ord-05149c9288364f2583be374274cc2755
Source dataset
uspto-grants-1998_03
Patent number
US05723667

Linked notes

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