Reaktion #347172

Reaktionsgleichung

2,3-dibromo-1-propene

phenylacetaldehyde

hydrochloric acid

→

2-bromo-5-phenyl-1-penten-4-ol

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react at the same temperature for 3 hours
2. 2
   Filtrationwere filtered off
3. 3
   Sonstigethe resultant filtrate was separated
4. 4
   WaschenThe organic phase was washed with a 7% sodium carbonate aqueous solution
5. 5
   workup.DISTILLATIONthe toluene was distilled off under reduced pressure
6. 6
   SonstigeThe resultant oily substance was purified by silica gel column chromatography

Vorschrift

49.93 Grams of 2,3-dibromo-1-propene were added dropwise to a mixture of 20.00 g of phenylacetaldehyde, 40 g of toluene, 60 g of 0.01% hydrochloric acid and 16.33 g of zinc powder at 30° C., and the mixture was allowed to react at the same temperature for 3 hours. After the reaction was completed, zinc-derived insolubles were filtered off, and the resultant filtrate was separated. The organic phase was washed with a 7% sodium carbonate aqueous solution, and the toluene was distilled off under reduced pressure. The resultant oily substance was purified by silica gel column chromatography to give 24.01 g of 2-bromo-5-phenyl-1-penten-4-ol; nD25 =1.536, FI-MS m/e 240(M+), 242(M+2+).

Quelle