Formaldehyde → Butanal, 4-(acetyloxy)-2-methylene-

HRID 376100Notes

Reaction equation

HRID 376100 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][O:6][C:7](=[O:9])[CH3:8].[Cl-].[CH3:11][NH2+]C.C=O>>[CH:2]([C:3](=[CH2:11])[CH2:4][CH2:5][O:6][C:7](=[O:9])[CH3:8])=[O:1]

Participants

4

Procedure

13.0 g (100 mmol) of acetic acid (4-oxo)butyl ester, 92.0 g (112.6 mmol) of dimethylammonium chloride and 10.8 ml (117 mmol) of 37% formaldehyde solution are heated at 100° for one hour with stirring. The mixture is allowed to cool and is extracted 3 times with 30 ml of diethyl ether each time. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated to dryness by evaporation. Acetic acid (3-formyl)but-3-enyl ester is obtained in the form of a colourless oil which can be reacted further without further purification.

Workup

  1. temperatureto cool
  2. extractionis extracted 3 times with 30 ml of diethyl ether each time
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness by evaporation

Sources & evidence

ORD record
ord-0fe41f32880b412c8f564555fb23e39e
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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