Propanal → 4,4-Diethoxy-2-methylbut-2-enal

HRID 373338Notes

Reaction equation

HRID 373338 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].CNC.C(O)(=O)CC.[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH:17]=O)[CH3:14]>O>[CH3:3][C:2](=[CH:17][CH:16]([O:19][CH2:20][CH3:21])[O:15][CH2:13][CH3:14])[CH:1]=[O:4]

Participants

6

Reactant 4

HCID 527PropanalHCID 674DimethylamineHCID 1032Propionic AcidHCID 2196092,2-Diethoxyacetaldehyde

Product 1

HCID 539058034,4-Diethoxy-2-methylbut-2-enalYield 68.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

504 g of a solution of 240 g of propionaldehyde in 264 g of diethoxyacetaldehyde (glyoxal(mono)diethylacetal) are run into a mixture of 48 g of dimethylamine in 72 g of water and 80 g of propionic acid at 40° C. in the course of 30 minutes, while stirring. The reaction mixture is then stirred for a further 3 hours. After the lower aqueous phase has been separated off, fractional distillation of the organic phase gives 237 g (68.9% of theory) of 2-methyl-4,4-diethoxybut-2-enal of boiling point 67°-69° C./8 mbar.

Workup

  1. stirringThe reaction mixture is then stirred for a further 3 hours
  2. customAfter the lower aqueous phase has been separated off
  3. distillationfractional distillation of the organic phase

Sources & evidence

ORD record
ord-6be4bf2a286240bfbe77497df2164ded
Source dataset
uspto-grants-1992_11
Patent number
US05162552

Reaction notes

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