Formaldehyde → 6-Acetoxy-2-methylene-hexanal

HRID 487483

Reaction equation

HRID 487483 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-1a81ca3a78c047d1b92a8006c8588c20
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Linked notes

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