Formaldehyde → 5-Acetoxy-2-methylenepentanal
Reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[O:10])(=[O:3])[CH3:2].[Cl-].[CH3:12][NH2+]C.C=O>>[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8](=[CH2:12])[CH:9]=[O:10])(=[O:3])[CH3:2]Participants
4
Procedure
10 g (69.4 mmol) of 5-acetoxypentanal, 6.37 g (78.2 mmol) of dimethylammonium chloride and 6.1 ml (81.2 mmol) of 37% formaldehyde solution are refluxed for 11/2 hours (bath temperature~110° C.) with stirring. The mixture is allowed to cool and is extracted three times with ether; the organic phases are combined, dried over MgSO4, filtered and concentrated by evaporation. 5-acetoxy-2-methylenepentanal is obtained in the form of a yellowish oil which can be reacted without further purification.
Workup
- temperatureto cool
- extractionis extracted three times with ether
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-b6531060dab546948e5781e89a8a69ae
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05294734
Reaction notes
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