Malonic Acid → 3-(2,4-Difluorophenyl)acrylic Acid

HRID 2207912Notes

Reaction equation

HRID 2207912 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 6035023-(2,4-Difluorophenyl)acrylic AcidYield 73.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Difluoro-benzaldehyde (10.0 g, 70.4 mmol), malonic acid (16.5 g, 158.3 mmol), and piperidine (5.8 mL, 58.4 mmol) were added to pyridine (42.7 mL). The reaction mixture was stirred at 100° C. for 2 hours, concentrated under reduced pressure, and then distilled water was added thereto. The mixture was filtered and then the resulting solid was dried under reduced pressure to give 9.5 g of the titled compound as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondistilled water was added
  3. filtrationThe mixture was filtered
  4. customthe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-2f036722771a4972843290516a887189
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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