Reaction #216207

Reaction equation

product

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

potassium hydroxide

hydrochloric acid

→

title product

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

Solvents

methanol

water

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed until a dark red solution
2. 2
   Otherformed
3. 3
   TemperatureThe mixture was cooled
4. 4
   Filtrationfiltered
5. 5
   Washthe solid residue washed thoroughly with water
6. 6
   Filtrationfiltered
7. 7
   OtherThe combined solid residues (500 mg) mp 200°-209°, were recrystallised from acetonitrile

Procedure

The product of stage (b) was suspended in 10 ml of boiling methanol and 0.55 g of potassium hydroxide in 5.5 ml of water was added dropwise over 15 mins. The mixture was refluxed until a dark red solution formed, (after ca. 6 hrs) when 2 ml of concentrated hydrochloric acid was cautiously added dropwise. The mixture was cooled and filtered, and the solid residue washed thoroughly with water. The water washings were re-acidified and filtered. The combined solid residues (500 mg) mp 200°-209°, were recrystallised from acetonitrile to give the title product as the trans-isomer (300 mg) m.p. 216°-219° C.

Source