(Z)-tetradec-9-en-1-ol

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: A process for preparing 9-tetradecenyl alcohol by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain tetradecenyl acetate and then reacting the acetate with water to obtain said alcohol.

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

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

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

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: A process for preparing 9-tetradecenyl alcohol by reacting 1-hexene or 5-decene with 9-decenyl acetate in accordance with the method of claim 7 to obtain tetradecenyl acetate and then reacting the acetate with water to obtain said alcohol.

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

Procedure: FIG. 18 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.

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

Procedure: A 2/1 trans to cis ratio of 9-tetradecenal was evaluated in the same manner as was used in the preceding example. The 9-tetradecenal was prepared from 9-tetradecenyl alcohol prepared in the same manner as described in the preceding example. About 21 grams of the alcohol in a 50/50 weight ratio selection of dichloromethane was added dropwise to a flask charged with 43 g (0.2 mol) pyridinium chlorochromate, 20 g celite and 200 mL dichloromethane. The mixture was stirred at room temperature for about 2 hours after addition of the alcohol solution was complete. Then 200 mL of hexane was added and the mixture was filtered. The solvent was evaporated and the product vacuum distilled through a 2 ft.×3/4 in. packed column (Penn State stainless steel packing). A 36% yield of pure 9-tetradecenyl acetate was obtained. prepared in the same manner the mixture was filtered The solvent was evaporated the product vacuum distilled through a 2 ft.×3/4 in

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

Procedure: FIG. 9 shows a synthesis of 9-tetradecenyl formate, in which 5-decene is cross-metathesized with 9-decenol in the presence of Grubbs' catalyst to produce 9-tetradecenol while 1-hexene is removed from the reaction under vacuum, and in which the metathesis product, 9-tetradecenol, is reacted with formyl acetate.