Reacción #1824329

Ecuación de reacción

2-hydroxy-naphthalene-1,4-dione

1-methylcyclohexanecarboxylic acid

ammonium peroxysulphate

→

2-hydroxy-3-(1-methyl-cyclohexyl)naphthalene-1,4-dione

Rendimiento 19.2%

Disolventes

diethyl ether

acetonitrile

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 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

To a stirred solution of 2-hydroxy-naphthalene-1,4-dione (1.00 g, 5.7 mmol), 1-methylcyclohexanecarboxylic acid (1.22 g, 8.6 mmol) and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. was slowly added a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) 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 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate. 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-methyl-cyclohexyl)naphthalene-1,4-dione (296 mg) as a yellow crystalline compound, m.pt.: 79° C.

Fuente