Butanal → Butanedioic acid, 2-(1-oxobutyl)-, 1,4-diethyl ester

HRID 1982118Notes

Reaction equation

HRID 1982118 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:13](=[O:17])[CH2:14][CH2:15][CH3:16]>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:13]([CH:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:1]([O:10][CH2:11][CH3:12])=[O:9])(=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 261ButanalHCID 5271566Diethyl Maleate

Product 1

HCID 170467Butanedioic acid, 2-(1-oxobutyl)-, 1,4-diethyl esterYield 85.6%

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

A mixture of 86 g of diethyl maleate, 144 g of butyraldehyde and 4 g of dibenzoyl peroxide was boiled at reflux for 20 hours. After completion of the reaction, the excess butyraldehyde was firstly distilled off over a Vigreux column and then the yellow coloured crude product was taken up in 250 ml of hexane and washed with 200 ml of 5% (wt./vol.) sodium hydrogen carbonate solution and 200 ml of water. The aqueous phases were back-extracted with a small amount of hexane. The combined organic phases were dried over sodium sulphate and freed from solvent on a rotary evaporator. Distillation of the resulting crude product in a high vacuum over a Vigreux column gave 104.5 g (85.6%) of diethyl 2-butyrylsuccinate as a slightly yellow coloured liquid; b.p. 84°-90° C./0.08 Torr.

Workup

  1. temperatureat reflux for 20 hours
  2. customAfter completion of the reaction
  3. distillationthe excess butyraldehyde was firstly distilled off over a Vigreux column
  4. washwashed with 200 ml of 5% (wt./vol.) sodium hydrogen carbonate solution and 200 ml of water
  5. extractionThe aqueous phases were back-extracted with a small amount of hexane
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. customfreed from solvent on a rotary evaporator
  8. distillationDistillation of the resulting crude product in a high vacuum over a Vigreux column

Sources & evidence

ORD record
ord-7dc81154cd174b0fb02129480c3f628c
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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