Methyl vinyl ketone → Propanedioic acid, (3-oxobutyl)-, dimethyl ester

HRID 1188305Notes

Reaction equation

HRID 1188305 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:14][CH3:15])(=[O:13])[CH2:8][C:9]([O:11][CH3:12])=[O:10].[CH:16]([C:18]([CH3:20])=[O:19])=[CH2:17].CC(OC)(C)C>O>[CH3:12][O:11][C:9](=[O:10])[CH:8]([CH2:17][CH2:16][C:18](=[O:19])[CH3:20])[C:7]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 6570Methyl vinyl ketoneHCID 7943Dimethyl malonateHCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl ether

Product 1

HCID 10035735Propanedioic acid, (3-oxobutyl)-, dimethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Potassium carbonate (5.62 kg), dimethyl malonate (54.8 kg) and acetonitirile (90 kg) were charged to the reaction vessel and stirred together at 15° C. Methyl vinyl ketone (28.5 kg) was pumped into the vessel over 2 hours at below 25° C. The slurry was stirred at 18-20° C. for 2 hours. MTBE (132 kg) was charged to the vessel to dilute the reaction mixture followed by water (114 kg). The mixture was stirred for five minutes then the layers were allowed to separate and the aqueous layer run off. More water (57 kg) was charged to the vessel, the reaction mixture stirred for another 5 minutes, the layers allowed to separate, and again the aqueous layer run off. The organic layer was concentrated under reduced pressure until most of the solvent had been removed (volume approx 80 L) affording 76 kg of A-1 as an oil.

Workup

  1. stirringThe slurry was stirred at 18-20° C. for 2 hours
  2. additionto dilute the reaction mixture
  3. stirringThe mixture was stirred for five minutes
  4. customto separate
  5. additionMore water (57 kg) was charged to the vessel
  6. stirringthe reaction mixture stirred for another 5 minutes
  7. customto separate
  8. concentrationThe organic layer was concentrated under reduced pressure until most of the solvent
  9. customhad been removed (volume approx 80 L)
  10. customaffording 76 kg of A-1 as an oil

Sources & evidence

ORD record
ord-18476b583b064fe4b54cce6a3b736ea4
Source dataset
uspto-grants-2014_03
Patent number
US08674093B2

Reaction notes

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