反应 #1824329

反应方程式

2-hydroxy-naphthalene-1,4-dione

1-methylcyclohexanecarboxylic acid

ammonium peroxysulphate

→

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

收率 19.2%

溶剂

diethyl ether

acetonitrile

water

water

反应条件

后处理

1. 1
   温度The mixture was heated for a further hour
2. 2
   其他The organic phase was separated
3. 3
   洗涤washed successively with water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
4. 4
   干燥before drying over magnesium sulphate
5. 5
   过滤Filtration and evaporation of the solvent under reduced pressure

实验过程

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.

来源