Lithium → 2-Nonenal

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence