Formaldehyde → 4-Acetoxy-2-methylene-pentanal

HRID 376168Notes

Reaction equation

HRID 376168 reaction equation
[C:1]([O:4][CH:5]([CH3:10])[CH2:6][CH2:7][CH:8]=[O:9])(=[O:3])[CH3:2].[Cl-].[CH3:12][NH2+]C.C=O>>[C:1]([O:4][CH:5]([CH3:10])[CH2:6][C:7](=[CH2:12])[CH:8]=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 111054874-AcetoxypentanalHCID 12954980Dimethylazanium;chloride

Product 1

HCID 189915204-Acetoxy-2-methylene-pentanalYield 93.9%

Procedure

18.0 g (124.8 mmol) of 4-acetoxypentanal, 11.5 g (140.7 mmol) of dimethylammonium chloride and 11.0 ml (146 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 then extracted three times with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated by evaporation, giving 18.3 g of 4-acetoxy-2-methylene-pentanal as a colourless oil which is further reacted without purification.

Workup

  1. temperatureto cool
  2. extractionextracted three times with CH2Cl2
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e332bc9677874c428220ed0e5d71f631
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

Loading…