Hydrochloric Acid → 3-(3-Fluorophenyl)-2-propenoic acid

HRID 1517146Notes

Reaction equation

HRID 1517146 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1.N1C=CC=CC=1.Cl>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 680093-Fluorobenzaldehyde

Product 1

HCID 886063-(3-Fluorophenyl)-2-propenoic acidYield 84%

Procedure

5 g (40.1 mmol) of 3-fluoro benzaldehyde, 8.38 g (2 eq.) of malonic acid, and 0.34 g (0.1 eq.) of piperidine were added to 9.52 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 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: 84%)

Workup

  1. temperatureAfter heating it to 80° C.
  2. stirringthe mixture was stirred for 12 hours
  3. customAfter the reaction
  4. temperaturethe resulting solution cooled to room temperature
  5. filtrationThe resulting powder was filtered
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-5c69cee21362490fa45773aba654871a
Source dataset
uspto-grants-2012_07
Patent number
US08231946B2

Reaction notes

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