Formaldehyde → 6-Acetoxy-2-methylene-hexanal

HRID 376149

Reaction equation

HRID 376149 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[O:11])(=[O:3])[CH3:2].[Cl-].[CH3:13][NH2+]C.C=O>>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[CH2:13])[CH:10]=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 69174896-Oxohexyl acetateHCID 12954980Dimethylazanium;chloride

Product 1

HCID 189915606-Acetoxy-2-methylene-hexanal

Procedure

16 g (101.1 mmol) of 6-acetoxyhexanal, 9.2 g (113 mmol) of dimethylammonium chloride and 9.2 ml (118.3 mmol) of a 37% solution of formaldehyde are stirred for 1 hour at a bath temperature of 110° C. The mixture is allowed to cool and extracted three times with CH2Cl2. The combined organic phases are dried over Na2SO4, filtered, and concentrated by evaporation giving 6-acetoxy-2-methylene-hexanal as a slightly yellowish 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 Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-201f78481e0b4b018808e9cfba22d1be
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Linked notes

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