Hydrochloric Acid → 3-(Pentafluorophenyl)prop-2-enoic acid

HRID 1517148Notes

Reaction equation

HRID 1517148 reaction equation
[F:1][C:2]1[C:7]([CH:8]=O)=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13].C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1.N1C=CC=CC=1.Cl>>[F:1][C:2]1[C:7]([CH:8]=[CH:15][C:16]([OH:18])=[O:17])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[F:13]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 69558Pentafluorobenzaldehyde

Product 1

HCID 5224353-(Pentafluorophenyl)prop-2-enoic acidYield 13%

Procedure

20 g (42 mmol) of pentafluoro-benzaldehyde, 21.23 g (2 eq.) of malonic acid, and 0.85 g (0.1 eq.) of piperidine were added to 24 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 was 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: 13%)

Workup

  1. temperatureAfter heating it to 80° C.
  2. stirringthe mixture was stirred for 12 hours
  3. customAfter the reaction
  4. temperaturethe resulting solution was 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-436d0e57087447dd88df59ee860f1c2c
Source dataset
uspto-grants-2012_07
Patent number
US08231946B2

Reaction notes

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