Sulfuric Acid → Hexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

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Reaction Steps

The carboxylic acid (51 g) prepared in Example 1 was slowly added with stirring to sulfuric acid (500 ml, 75 percent by volume). The exothermic reaction that ensued was controlled by an ice-water bath. The reaction subsided after several minutes and the resulting dark solution was then kept at room temperature for about 10 days. The solution was then poured into ice-water (150 ml) and the product then extracted with diethyl ether (three 200-ml portions). The combined extracts were washed with saturated sodium bicarbonate solution (200 ml). The ether was evaporated yielding 45.5 g of 6-oxatricyclo[3.2.1.13,8 ]nonan-7-one which was about 91 percent of theory. The product was identified by GC-mass spectrometric, infrared and melting point analysis.

Provenance & Evidence