Reacción #10248

Ecuación de reacción

1,3-cyclohexadiene

isoamyl nitrite

anthranilic acid

→

1,4-dihydro-1,4-ethanonaphthalene

Rendimiento 78.0%

Disolventes

tetrahydrofuran

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 2 hours
2. 2
   Otroto remove THF
3. 3
   Extracciónextracted with chloroform
4. 4
   Lavadowashed with distilled water and saturated saline
5. 5
   Secadodried with anhydrous sodium sulfate
6. 6
   Otropurified with silica gel column-chromatography-(chloroform)

Procedimiento

A THF solution of 1 g (7.3 mmol) of anthranilic acid was dropped into a mixed solution under reflux of 0.77 ml (8.0 mmol) of 1,3-cyclohexadiene, 1.1 ml of isoamyl nitrite and 50 ml of tetrahydrofuran. Then, the resultant solution was heated and refluxed for 2 hours to remove THF, extracted with chloroform, washed with distilled water and saturated saline, dried with anhydrous sodium sulfate and purified with silica gel column-chromatography-(chloroform) to obtain 1,4-dihydro-1,4-ethanonaphthalene (0.89 g, 5.7 mmol, yield: 78%).

Fuente