Reaction #2329011

Reaction equation

1,3-Cyclohexanediol

acetonitrile

potassium fluoride on alumina

4-fluoro-2-chloro-benzonitrile

→

title compound

Yield 8.7%

2-Chloro-4-(3-hydroxy-cyclohexyloxy)-benzonitrile

Yield 8.7%

Solvents

Diethyl ether

Conditions

Workup

1. 1
   Otherdried round bottom flask under nitrogen
2. 2
   Temperatureheated
3. 3
   Temperatureat reflux for 16 h
4. 4
   Extractionwas then extracted with water (2×)
5. 5
   Dryingdried (MgSO4)
6. 6
   Concentrationconcentrated
7. 7
   OtherPurification
8. 8
   Washeluting with 10% EtOAc/hex (ethylacetate and hexane)

Procedure

1,3-Cyclohexanediol (116 mg, 1.0 mmole) was added to a flame dried round bottom flask under nitrogen. The flask was then charged with 5 mL of dry acetonitrile, 26 mg of potassium fluoride on alumina (0.1 mmol), and 4-fluoro-2-chloro-benzonitrile (155 mg, 1.0 mmole) and heated at reflux for 16 h. Diethyl ether (15 ml) was added to the reaction mixture, which was then extracted with water (2×), dried (MgSO4) and concentrated. Purification using a chromatotron, eluting with 10% EtOAc/hex (ethylacetate and hexane) provided 22 mg of the title compound. GC/MS: 251 (M/Z for C13H14ClNO2).

Source