Reaction #1884998

Reaction equation

4-fluoro-cinnamic acid

5-norbornene-2-methanol

toluene

→

5-norbornene 2-methyl-(4-fluoro-cinnamate)

Yield 68.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperatureazeotropically refluxed for 24 hours
2. 2
   OtherAfter the reaction
3. 3
   Temperaturethe mixture cooled down to room temperature
4. 4
   ExtractionThe resulting product was extracted with 1M HCl
5. 5
   Washwashed again with water
6. 6
   DryingThe organic layer was dried with Na2SO4
7. 7
   Otherthe solvent was evaporated out
8. 8
   Otherto give a highly viscous material

Procedure

10 g (60 mmol) of 4-fluoro-cinnamic acid, 7.45 g (60 mmol) of 5-norbornene-2-methanol, and 0.3 g (0.02 eq.) of zirconium(IV) acetate hydroxide were added to 50 ml of toluene and stirred. The mixture was heated to 145° C. under N2 atmosphere and azeotropically refluxed for 24 hours. After the reaction, the mixture cooled down to room temperature and was added with 100 volume % of ethyl acetate. The resulting product was extracted with 1M HCl and washed again with water. The organic layer was dried with Na2SO4 and the solvent was evaporated out to give a highly viscous material. (Yield: 68%, Purity (GC): 92%)

Source