Sulfuric Acid → 10-Cycloeicosenone

Participants

Reaction Conditions

Reaction Steps

In a 50 ml four neck reactor equipped with a thermometer, a dripping funnel and a refrigerant, zinc powder (2.3 g), 2-hydroxy-11-cycloeicosenone (1.4 g) and toluene (10 ml) were mixed, stirred and heated at 90° C. under a nitrogen flow. A 20N sulphuric acid aqueous solution (2.8 ml) was added thereto dropwise over 2.5 hours, and the resulting mixture was stirred under heating for 30 minutes. After the reaction, the mixture was supplemented with toluene and water, and allowed to stand to separate into two phases. The organic phase thus obtained was washed twice with water and then with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure to give 1.4 g of crude product. This latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1, v/v) to give 1.2 g of 10-cycloeicosenone (yield 92%).

Provenance & Evidence