Reaction #216206

Reaction equation

ammonium persulphate

2-chloro-1,4-naphthoquinone

4-(4-chlorophenyl)cyclohexane-1-carboxylic acid

→

solid

Yield 35.0%

2-[4-(4-chlorophenyl)cyclohexyl]-3-Chloro-1,4-naphthoquinone

Yield 35.0%

Solvents

acetonitrile

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux
3. 3
   TemperatureThe mixture was refluxed for 3 hours
4. 4
   Temperaturethen cooled in ice for 30 mins
5. 5
   Filtrationafter which it was filtered
6. 6
   Extractionthe residual sticky solid extracted twice with boiling chloroform
7. 7
   Otherto remove inorganic material
8. 8
   OtherThe chloroform was removed by evaporation

Procedure

A mixture of 2-chloro-1,4-naphthoquinone (3.95 g, 0.02 mol), 4-(4-chlorophenyl)cyclohexane-1-carboxylic acid (4.9 g, 0.02 mol) and powdered silver nitrate (1.05 g, 0.0062 mol) was heated to reflux with vigorous stirring in 40 ml of acetonitrile. A solution of ammonium persulphate (12.0 g, 0.0525 mol) in 50 ml of water was added dropwise over 1 hour. The mixture was refluxed for 3 hours then cooled in ice for 30 mins, after which it was filtered, and the residual sticky solid extracted twice with boiling chloroform to remove inorganic material. The chloroform was removed by evaporation to leave a yellow-brown solid (ca 2.7 g). This was dissolved in 40 ml of boiling acetonitrile; a little insoluble material was removed by filtration. On cooling, the title compound separated as yellow crystals, (550 mg) m.p. 172°-175° C.

Source