Sulfuric Acid → 10-Cycloeicosenone

Temperature

90 °C

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%).

1. stirringthe resulting mixture was stirred
2. temperatureunder heating for 30 minutes
3. customAfter the reaction
4. customto separate into two phases
5. customThe organic phase thus obtained
6. washwas washed twice with water
7. customThe solvent was removed under reduced pressure
8. customto give 1.4 g of crude product
9. customThis latter was purified on a silica gel column chromatography (hexane/ethyl acetate=10/1

ORD record

ord-a68d66c72050437faeaba63c2ae9b3ae

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759557B2