Anthranilic Acid → 1,4-Ethanonaphthalene, 1,4-dihydro-

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Reaction Steps

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%).

Provenance & Evidence