Formaldehyde → 4-Ethoxycarbonylmethoxy-2-methylene-butanal

HRID 487493Notes

Reaction equation

HRID 487493 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 CH2Cl2The 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 CH2Cl2The combined organic phases
  3. dry with materialare dried over Na2SO4
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4b49505d15e6420783387904e58b55c1
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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