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

HRID 376137Notes

Reaction equation

HRID 376137 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH3:15][NH2+]C.C=O>>[CH2:1]([O:8][CH2:9][CH2:10][C:11](=[CH2:15])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 2315594-BenzyloxybutanalHCID 12954980Dimethylazanium;chloride

Product 1

HCID 10932234Butanal, 2-methylene-4-(phenylmethoxy)-

Procedure

8.0 g (44.9 mmol) of 4-benzyloxybutanal, 4.12 g (50.6 mmol) of dimethylammonium chloride and 3.95 ml (52.6 mmol) of 37% formaldehyde solution are kept at a bath temperature of 110° for one hour with stirring. The mixture is allowed to cool and is extracted three times with ether. The organic phases are washed with saturated sodium chloride solution, combined, dried over MgSO4, filtered and concentrated by evaporation. 4-benzyloxy-2-methylenebutanal is obtained in the form of a yellowish oil which can be reacted further without further purification.

Workup

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

Sources & evidence

ORD record
ord-e4e5468ca4104247aa76852350049e30
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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