Hydrochloric Acid → pentane-2,3,4-trione 4-(O-methyl oxime)-2-oxime

HRID 1636957Notes

Reaction equation

HRID 1636957 reaction equation
[N:1](OCCCC)=[O:2].C[O-].[Na+].[CH3:11][O:12][N:13]=[C:14]([C:16](=[O:19])[CH2:17][CH3:18])[CH3:15].Cl>CO>[CH3:11][O:12][N:13]=[C:14]([CH3:15])[C:16](=[O:19])[C:17](=[N:1][OH:2])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10996Butyl nitriteHCID 10942334Sodium MethoxideHCID 541960112,3-Pentanedione, 2-(O-methyloxime)

Product 1

HCID 53804423pentane-2,3,4-trione 4-(O-methyl oxime)-2-oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10.3 g (0.1 mol) of n-butyl nitrite and then 54 g of a 30% strength solution of sodium methylate in methanol are carefully added dropwise at 10° C. to a solution of 12.9 g (0.1 mol) of pentane-2,3-dione 2-(O-methyl oxime) in 120 ml of methanol. The mixture is allowed to come to room temperature and is stirred for 12 hours at this temperature. The mixture is worked up by adding dilute hydrochloric acid to a pH of 7 and subsequent evaporation in vacuo. The residue is taken up in 100 ml of water and extracted twice using in each case 100 ml of diethyl ether. The organic phase is dried over sodium sulfate and evaporated in vacuo. This gives 7.7 g (49%) of an oil.

Workup

  1. customto come to room temperature
  2. customto a pH of 7 and subsequent evaporation in vacuo
  3. extractionextracted twice
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-df02c1ebe0e344c59a8f14993dc8e8e5
Source dataset
uspto-grants-2000_03
Patent number
US06037378

Reaction notes

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