Water → Dimethyl n-hexylmalonate

HRID 1609355Notes

Reaction equation

HRID 1609355 reaction equation
C[O-].[Na+].[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].O>CO>[CH2:14]([CH:5]([C:4]([O:11][CH3:12])=[O:10])[C:6]([O:8][CH3:9])=[O:7])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 81011-BromohexaneHCID 10942334Sodium Methoxide

Product 1

HCID 2784953Dimethyl n-hexylmalonateYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

350.1 g of 30 percent sodium methylate solution in methanol were diluted with 550 ml of methanol under nitrogen and while stirring. 264.2 g of dimethyl malonate were added dropwise. After warming the suspension to 4020 321.0 g of 1-bromohexane were added dropwise. After stirring at 40° for 1 hour, under reflux for 2 hours, at 65°-69° for 2.5 hours and cooling the suspension to room temperature water was added and the mixture was stirred. The organic phase was separated. The aqueous phase was extracted with methylene chloride, the combined organic extracts were dried and filtered, the filter cake was washed with methylene chloride and the combined filtrates were concentrated. After distillation of the product there were obtained 329.3 g (78.3%) of dimethyl n-hexylmalonate.

Workup

  1. additionwere added dropwise
  2. stirringAfter stirring at 40° for 1 hour
  3. temperatureunder reflux for 2 hours, at 65°-69° for 2.5 hours
  4. additionwas added
  5. stirringthe mixture was stirred
  6. customThe organic phase was separated
  7. extractionThe aqueous phase was extracted with methylene chloride
  8. customthe combined organic extracts were dried
  9. filtrationfiltered
  10. washthe filter cake was washed with methylene chloride
  11. concentrationthe combined filtrates were concentrated
  12. distillationAfter distillation of the product there

Sources & evidence

ORD record
ord-fc1807269e3e4c0c8d436455d4acf226
Source dataset
uspto-grants-1995_03
Patent number
US05399720

Reaction notes

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