Carbon Dioxide → 3-(4-Difluoromethoxy-phenyl)-acrylic acid

HRID 2113864Notes

Reaction equation

HRID 2113864 reaction equation
[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[F:1][CH:2]([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 2736986p-(Difluoromethoxy)benzaldehyde

Product 1

HCID 7039363-(4-Difluoromethoxy-phenyl)-acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 10.0 g (7.68 ml, 58.1 mmol) 4-difluoromethoxy-benzaldehyde, 6.65 g (63.9 mmol) malonic acid, 0.21 g (2.50 mmol) piperidine and 50 ml pyridine was kept at reflux temperature until carbon dioxide development ceased (3 h). After cooling to room temperature the reaction mixture was poured onto 200 g ice and 100 ml 6N HCl. The precipitate was isolated, washed with water and dried. Yield: 8.8 g (71%) 3-(4-Difluoromethoxy-phenyl)-acrylic acid.

Workup

  1. custom(3 h)
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8c12ae220ac44589bb061e02b9df09c5
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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