Hydrochloric Acid → 3-(3,4-Difluorophenyl)prop-2-enoic acid

HRID 1517147Notes

Reaction equation

HRID 1517147 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.N1C=CC=CC=1.Cl>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[CH:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 5880883,4-Difluorobenzaldehyde

Product 1

HCID 1454863-(3,4-Difluorophenyl)prop-2-enoic acidYield 95%

Procedure

10 g (70.4 mmol) of 3,4-di-fluoro-benzaldehyde, 14.65 g (2 eq.) of malonic acid, and 0.59 g (0.1 eq.) of piperidine were added to 16.7 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: 95%)

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 down to room temperature
  5. filtrationThe resulting powder was filtered
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-fe29b22d98874d8ea55bab60fe628c00
Source dataset
uspto-grants-2012_07
Patent number
US08231946B2

Reaction notes

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