Acetic Acid → HCID 85757965, compound

HRID 343634Notes

Reaction equation

HRID 343634 reaction equation
C(O)(=O)C.[C:5]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])(=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:8].[N:20]([O-])=[O:21].[Na+].C([O-])(=O)C.[Na+]>C(OC)(C)(C)C.O.O1CCOCC1>[OH:21][N:20]=[C:6]([C:7]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:8])[C:5]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 3016555Diisobutyl malonateHCID 23668193Sodium Nitrite

Product 1

HCID 85757965HCID 85757965, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Procedure

112.2 of acetic acid (96%) were added dropwise over 2 hours to a stirred mixture of 216.0 g (1 mol) of diisobutyl malonate, 250 g of 1,4-dioxane, 25.6 g of deionized water ad 80 g (1.15 mol) of sodium nitrite (technical grade), maintained at from 35° to 40° C. The mixture was allowed to continue reacting for 2 hours at 50° C., then 35.0 g of anhydrous sodium acetate and 200 g of methyl tert-butyl ether were added. After cooling of the mixture, the precipitated coarsely-crystalline sodium acetate trihydrate was filtered off and washed using methyl tert-butyl ether. Removal of the low-boilers by distillation at 60° C. under water-pump vacuum gave 258.7 g (88.6% of theory) of residue comprising primarily diisobutyl hydroxyiminomalonate. The content of unconverted diisobutyl malonate was 0.4 FID aea percent.

Workup

  1. temperaturemaintained at from 35° to 40° C
  2. temperatureAfter cooling of the mixture
  3. filtrationthe precipitated coarsely-crystalline sodium acetate trihydrate was filtered off
  4. washwashed
  5. customRemoval of the
  6. distillationlow-boilers by distillation at 60° C. under water-pump vacuum

Sources & evidence

ORD record
ord-7cad827d88154d59b59eb393320e4006
Source dataset
uspto-grants-1999_01
Patent number
US05861533

Reaction notes

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