Réaction #10248

Équation de réaction

1,3-cyclohexadiene

isoamyl nitrite

anthranilic acid

→

1,4-dihydro-1,4-ethanonaphthalene

Rendement 78.0%

Solvants

tetrahydrofuran

THF

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 2 hours
2. 2
   Autreto remove THF
3. 3
   Extractionextracted with chloroform
4. 4
   Lavagewashed with distilled water and saturated saline
5. 5
   Séchagedried with anhydrous sodium sulfate
6. 6
   Autrepurified with silica gel column-chromatography-(chloroform)

Mode opératoire

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%).

Source