Benzal chloride → 1-Chloro-5-decene

Participants

Reaction Steps

1-Chloro-5-decene was synthesized as follows: 200.1 g (1.61 mol 95% pure) of 1-chloro-5-hexene, 282 g (416 mL, 3.35 mol) of 1-hexene and 2.0 mL of α,α-dichlorotoluene (metal hydride inhibitor) were added to a dry 1-L 2-necked round-bottomed flask containing a reflux condenser and a stir bar. This mixture was sparged sub-surface with Argon. After 10 minutes 5.5 g (6.67 mol) of the metathesis catalyst of Example 1 was added. The mixture was placed in a 62° C. oil bath and stirred. Samples were taken periodically and analyzed by gas chromatography (GC) to determine the extent of conversion. After 3 hours, the reaction stopped and the catalyst was inactivated by the addition of 3 mL of ethyl vinyl ether. The catalyst was removed by filtering the mixture through 200 g of silica gel. The silica gel was rinsed with 500 mL of hexane and combined with the post-filtered reaction solution. 1-chloro-5-decene was purified by vacuum distillation to yield 105.9 g. This was converted to 5-decenyl acetate as follows.

Provenance & Evidence