Ethylenediamine → 4-Octen-3-one

HRID 262076

Reaction equation

HRID 262076 reaction equation
[CH2:1]([CH2:6][C:7]([CH:9]=[C:10](C)C)=[O:8])[CH:2]=[C:3](C)[CH3:4].C(N)CN.[OH-].[Na+]>>[CH3:10][CH2:9][C:7](=[O:8])[CH:6]=[CH:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 132449842,8-Dimethylnona-2,7-dien-4-one

Product 1

HCID 842164-Octen-3-oneYield 95.8%

Procedure

A 500 ml flask was charged with 100.0 g of prenyl mesityl oxide (13% nonconjugated 79.7% conjugated isomer), 0.56 mole, 40.6 g ethylene diamine, and 0.5 g NaOH. This was then flushed thoroughly with nitrogen. The mixture was heated at between 95° and 105° C. and agitated for approximately four hours under a slight nitrogen pressure. Analysis by gas liquid chromatography indicated that 31.9% prenyl mesityl oxide remained unchanged after this time. Steam distillation of the pot mixture gave a true yield of 95.8% of methyl heptenone based on the prenyl mesityl oxide reacted, after the recovery of unreacted prenyl mesityl oxide.

Workup

  1. customThis was then flushed thoroughly with nitrogen
  2. temperatureThe mixture was heated at between 95° and 105° C.
  3. distillationSteam distillation of the pot mixture

Sources & evidence

ORD record
ord-b6eefbb5675d4d5fa52ef55c81be5471
Source dataset
uspto-grants-1979_05
Patent number
US04153633

Linked notes

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