Reacción #1824328

Ecuación de reacción

2-hydroxynaphthalene-1,4-dione

acetonitrile

ammonium peroxysulphate

→

2-hydroxy-3-(1-methylcyclopentyl)naphthalene-1,4-dione

Disolventes

diethyl ether

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated for a further hour
2. 2
   OtroThe organic phase was separated
3. 3
   Lavadowashed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
4. 4
   Secadobefore drying over magnesium sulphate
5. 5
   FiltraciónFiltration and evaporation of the solvent under reduced pressure

Procedimiento

A 50% excess of this acid was added to a stirred solution of 2-hydroxynaphthalene-1,4-dione (1.00 g, 5.7 mmol), and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. and a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) was slowly added to that over a period of 15 minutes. The mixture was heated for a further hour before cooling to room temperature (about 20° C.) and diluting with diethyl ether (50 ml). The organic phase was separated and washed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate as set out in Example 3. Filtration and evaporation of the solvent under reduced pressure followed by silica gel column chromatography using 2:1 petrol:diethyl ether as eluant gave 2-hydroxy-3-(1-methylcyclopentyl)naphthalene-1,4-dione (mp 116-118° C.).

Fuente