Bromoethene → Nerolidol

Participants

Reaction Steps

According to the method reported by A. Ofner et al in Helv. Chim. Acta., 42, 2577-2584 (1959), cis- or trans-nerolidol was prepared respectively from cis- or trans-geranylacetone. That is, in 420 ml. of tetrahydrofuran were placed 12.5 g. of freshly-prepared metallic magnesium turnings and 60 g. of vinyl bromide were added dropwise thereto under water cooling to form a Grignard reagent. 50 g. cis- or trans-geranylacetone were added dropwise thereto at 25° C. The reaction mixture was neutralized with ammonium chloride and extracted with ether. The extract was dried over sodium sulfate and distilled off under reduced pressure. The residue was subjected to vacuum distillation (1.0 mmHg) in a rectifying column having about 40 theoretical plates (about 30 practical plates) with a reflux ratio of 10 ~ 20 and a bottom temperature of approximately 190° C., to give cis-nerolidol from cis-geranylacetone in a yield of 82 percent. The product was identified by the standard product obtained in Example 12. The trans-isomer was obtained in the same manner.

Provenance & Evidence