Benzal chloride → 1-Nonene, 9-chloro-

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Reaction Steps

The so-produced nonenyl chloride (112 g; 700 mmol) was added to an equimolar amount of the 2,4-hexadiene in a 100 mL round-bottomed flask equipped with a magnetic stir bar and a reflux condenser, along with 6 g of α,α-dichlorotoluene. This solution was subsurface-sparged with nitrogen for 10 minutes. The catalyst of Example 1 (1.15 g; 1.4 mmol) was added and the reaction flask was placed in an 85° C. oil bath for 15 hours. The reaction was terminated by cooling to room temperature, followed by the addition of 300 ml of hexanes and filtering three times through 75 g of silica gel. Hexanes were removed under reduced pressure and the remaining liquid was vacuum distilled through a 2 cm×30 cm packed bed column to yield 12 g of 8-nonen-1-yl chloride (Bpt1.5 36-40° C.), 46.3 g of 8-decen-1-yl chloride (Bpt1.5 56-60° C.), 15.3 g of 8,10-dodecadien-1-yl chloride (Bpt1.5 90-91 C.), and 30.4 g of 76% purity 1,16-dichloro-8-hexadecene and high boilers that remained in the distillation pot.

Provenance & Evidence