Dichloromethane → 9-Tetradecen-1-ol, acetate

Participants

Reaction Steps

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.

Provenance & Evidence