Formaldehyde → 4-Benzoyloxy-2-methylenebutanal

HRID 487468Notes

Reaction equation

HRID 487468 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH3:16][NH2+]C.C=O>>[C:1]([O:9][CH2:10][CH2:11][C:12](=[CH2:16])[CH:13]=[O:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 110087524-Oxobutyl benzoateHCID 12954980Dimethylazanium;chloride

Product 1

HCID 189915294-Benzoyloxy-2-methylenebutanal

Procedure

10 g (52 mmol) of 4-benzoyloxybutanal, 4.78 g (58.6 mmol) of dimethylammonium chloride and 4.6 ml (60.8 mmol) of formaldehyde solution (37%) are refluxed for one hour with stirring (bath temperature ~110° C.). The mixture is allowed to cool and is extracted three times with ether; the organic phases are combined, washed with saturated sodium chloride solution, dried over MgSO4, filtered and concentrated by evaporation. 4-benzoyloxy-2-methylenebutanal is obtained in the form of a yellowish oil which can be reacted without further purification.

Workup

  1. temperatureto cool
  2. extractionis extracted three times with ether
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-75915d019b444692b1cbc9f1df203d57
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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