Methanol → Propanedioic acid, dimethoxy-, dimethyl ester

HRID 487010Notes

Reaction equation

HRID 487010 reaction equation
[CH3:1][O-:2].[Na+].[Na].Br[CH:6]([C:12]([O:14][CH2:15]C)=[O:13])[C:7]([O:9][CH2:10]C)=[O:8].[CH3:17][OH:18]>C(OCC)C>[CH3:1][O:2][C:6]([O:18][CH3:17])([C:12]([O:14][CH3:15])=[O:13])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 69637Diethyl bromomalonateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 12231544Propanedioic acid, dimethoxy-, dimethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of sodium methoxide prepared by dissolving 5.75 grams (0.25 mole) of sodium in 375 milliliters of anhydrous methanol was added 59.8 grams (0.25 mole) of diethyl bromomalonate in one portion and the resulting mixture heated under reflux for 4 hours. The mixture was freed of methanol solvent under reduced pressure and the residue taken up in ethyl ether and filtered to remove by-product solids. The filtrate was freed of ether under reduced pressure and the residue vacuum distilled In a short-path system to give 6.49 grams (0.03 mole) of dimethyl dimethoxymalonate boiling over a range of 100° C.-125° C. at 1.4-1.8 Mm of Hg. NMR analysis of the product indicated the following:

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 4 hours
  3. filtrationfiltered
  4. customto remove by-product solids
  5. distillationthe residue vacuum distilled In a short-path system

Sources & evidence

ORD record
ord-2ee2d0fd3ab14adbb4590c0fcd1c0488
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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