Lithium → (E)-2-Nonenal

HRID 1657942Notes

Reaction equation

HRID 1657942 reaction equation
[C:1](Cl)(=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Li]>COCCOCCOC>[CH:1](=[O:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 12575251HCID 12575251, compound

Product 1

HCID 5283335(E)-2-Nonenal

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Conditions

Temperature
-78 °C

Procedure

Trans-2-nonenoyl chloride (170 g, 1 mole) is dissolved in 500 ml of diglyme and placed in a flask fitted with a mechanical stirrer, dripping funnel, low temperature thermometer and nitrogen inlet and outlet. The flask is flushed with nitrogen and cooled to -78°C in a dry ice acetone bath. To the flask, lithium tri-t-butoxyaluminohydried (254 g, 1 mole) in 1000 ml of diglyme is added over a period of 7 hours. The cooling bath is removed and the contents of the flask are allowed to warm to room temperature. The contents are poured onto crushed ice and the oily layer taken up in ether. The ether solution is dried over sodium sulfate, concentrated and vacuum distilled to give trans-2-nonenal.

Workup

  1. customplaced in a flask
  2. customfitted with a mechanical stirrer
  3. customThe flask is flushed with nitrogen
  4. customThe cooling bath is removed
  5. temperatureto warm to room temperature
  6. additionThe contents are poured
  7. customonto crushed ice
  8. dry with materialThe ether solution is dried over sodium sulfate
  9. concentrationconcentrated
  10. distillationvacuum distilled

Sources & evidence

ORD record
ord-444a83e2455c49cbb22f985f85b6fe9b
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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