Ethanol → 1,4-Diethyl 2-formylbutanedioate

HRID 1085696

Reaction equation

HRID 1085696 reaction equation
[CH2:1]([OH:3])C.[Na].[C:5]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C(OCC)=O>C1(C)C=CC=CC=1.O>[CH:1]([CH:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([O:14][CH2:15][CH3:16])=[O:13])=[O:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 31249Diethyl SuccinateHCID 5360545Sodium

Product 1

HCID 2315001,4-Diethyl 2-formylbutanedioate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Ethanol (20 cm3) was added portionwise to a suspension of finely divided sodium (10.0 g) in dry toluene (100 cm3). On completion of the addition the mixture was heated for 3.5 hours at 80° C. To the resulting yellow suspension, cooled to 20° C., was added dropwise, over a period of 1 hour, a mixture of diethyl succinate (70.0 g) and ethyl formate (35.0 g), whilst the temperature of the mixture was maintained in the range 20° to 30° C. The mixture was kept at the ambient temperature for 16 hours after which water (100 cm3) was added carefully.

Workup

  1. additionOn completion of the addition the mixture
  2. temperatureTo the resulting yellow suspension, cooled to 20° C.
  3. additionwas added dropwise, over a period of 1 hour
  4. temperaturewhilst the temperature of the mixture was maintained in the range 20° to 30° C

Sources & evidence

ORD record
ord-a703ade16f59445d853f4896ce6e4402
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Linked notes

Loading…