Diethyl Malonate → Propanedioic acid, 2-(1-ethoxyethylidene)-, 1,3-diethyl ester

HRID 2248980Notes

Reaction equation

HRID 2248980 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12](OCC)(OCC)([O:14][CH2:15][CH3:16])[CH3:13]>>[C:1]([C:2](=[C:12]([O:14][CH2:15][CH3:16])[CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])([O:9][CH2:10][CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 66221Triethyl orthoacetate

Product 1

HCID 99520Propanedioic acid, 2-(1-ethoxyethylidene)-, 1,3-diethyl esterYield 73%

Conditions

Temperature
159 °C

Procedure

160 g (1 mol) of diethyl malonate, 649 g (4 mol) of triethyl orthoacetate and 0.5 g of catalyst from Example 1 were heated to 130° C. in a glass apparatus having a distillation column. The metering-in of 102 g of acetic anhydride over the course of 7 h was then begun. The bottom temperature was increased to 159° C. with the distillation of low-boiling components at a head temperature of 72° to 73° C. After the end of the reaction, the residual low-boiling components were distilled off under a low vacuum and the excess triethyl orthoacetate was removed at 15 mbar. The desired product was then distilled over at 0.3 mbar and a head temperature of 100° to 102° C. Ethyl 2-carboethoxy-3-ethoxy-2-butenoate was obtained in a yield of 73% of the theoretical yield.

Workup

  1. distillationa distillation column
  2. customover the course of 7 h
  3. customAfter the end of the reaction
  4. distillationthe residual low-boiling components were distilled off under a low vacuum
  5. customthe excess triethyl orthoacetate was removed at 15 mbar
  6. distillationThe desired product was then distilled over at 0.3 mbar
  7. customa head temperature of 100° to 102° C

Sources & evidence

ORD record
ord-7a1855e627704ecc969dcc1ff118b328
Source dataset
uspto-grants-1991_08
Patent number
US05041619

Reaction notes

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