Formaldehyde → 4-Ethoxycarbonylmethoxy-2-methylene-butanal

HRID 376159Notes

Reaction equation

HRID 376159 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH:11]=[O:12])=[O:5])[CH3:2].[Cl-].[CH3:14][NH2+]C.C=O>>[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][C:10](=[CH2:14])[CH:11]=[O:12])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 12954980Dimethylazanium;chlorideHCID 189915874-Ethoxycarbonylmethoxybutanal

Product 1

HCID 189915804-Ethoxycarbonylmethoxy-2-methylene-butanal

Procedure

11 g (63.1 mmol) of 4-ethoxycarbonylmethoxybutanal, 5.8 g (71.4 mmol) of dimethylammonium chloride and 5.5 ml (73.5 mmol) of a 37% solution of formaldehyde are stirred for 1 hour at a bath temperature of 110° C. The reaction mixture is allowed to cool and extracted three times with CH2Cl2. The combined organic phases are dried over Na2SO4 and concentrated by evaporation giving 4-ethoxycarbonylmethoxy-2-methylene-butanal as a yellowish liquid which is further reacted without purification.

Workup

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-89c1888346644a5bba3c894730438b7d
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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