Reaction #1884993

Reaction equation

4-fluoro-benzaldehyde

malonic acid

piperidine

pyridine

HCl

→

4-fluoro-cinnamic acid

Yield 90.0%

Conditions

Workup

1. 1
   TemperatureAfter heating it to 80° C.
2. 2
   workup.STIRRINGthe mixture was stirred for 12 hours
3. 3
   OtherAfter the reaction
4. 4
   Temperaturethe resulting solution cooled down to room temperature
5. 5
   FiltrationThe resulting powder was filtered
6. 6
   Washwashed with water
7. 7
   Otherdried in a vacuum oven

Procedure

10 g (80.6 mmol) of 4-fluoro-benzaldehyde, 29.5 g (2 eq.) of malonic acid, and 1.21 g (0.1 eq.) of piperidine were added to 33.7 g (3 eq.) of pyridine and stirred at room temperature for about 1 hour. After heating it to 80° C., the mixture was stirred for 12 hours. After the reaction, the resulting solution cooled down to room temperature and was slowly added with 1M HCl until it was titrated to about pH 4. The resulting powder was filtered and washed with water, and then dried in a vacuum oven. (Yield: 90%)

Source