6-chlorohex-1-ene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The procedure of Example 1 was repeated with minor changes. 51.0 g of 6-chloro-1-hexene (Aldrich) and 35.3 g of 1-methylimidazole (Aldrich) were added into a 2000 ml three-neck round-bottom flask. The reaction temperature was set from 75 to 80° C. After four hours the milk-like solution transferred into a homogenous solution. The reaction was continued for three days. Then, the product was washed with ethyl acetate five times. After that, it was dried under vacuum for three days. was set from 75 to 80° C The reaction was continued for three days Then, the product was washed with ethyl acetate five times After that, it was dried under vacuum for three days

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. containing a reflux condenser and a stir bar This mixture was sparged sub-surface with Argon was placed in a 62° C. The catalyst was removed by filtering the mixture through 200 g of silica gel The silica gel was rinsed with 500 mL of hexane combined with the post-filtered reaction solution 1-chloro-5-decene was purified by vacuum distillation to yield 105.9 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Peach Twig Borer (PTB) pheromone is a mixture of 5-decenyl acetate and 5-decenol of approximately 85:15 molar ratio of the acetate to the alcohol. The synthesis of PTB pheromoneqcouples 1-chloro-5-hexene and 1-hexene to yield 1-chloro-5-decene. 1-chloro-5-decene is converted to 5-decenyl acetate, isomerized and a portion of the acetate is hydrolyzed to the corresponding alcohol to yield PTB pheromone. The overall scheme using the catalyst of Example 1 is shown below, followed by details of the synthesis. ##STR1##

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, 50 ml of sodium hypochlorite solution (12.5% of active chlorine, admixed with a spatula tip of sodium acetate) were added dropwise with vigorous stirring to a solution of 15 g (51.4 mmol) of 3-bromo-2-methyl-6-methylsulfonylbenzaldehyde oxime and 6.7 g (56.5 mmol) of 6-chlorohexene in 200 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then stirred into 300 ml of water. The organic phase was washed three times with water, dried and concentrated to dryness. This gave 19.3 g of a viscous yellow oil (92.4% of theory). The 1H-NMR spectrum corresponds to the given structure. At room temperature were added dropwise The organic phase was washed three times with water dried concentrated to dryness