Carbon Dioxide → 3-[4-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic Acid

HRID 1271427Notes

Reaction equation

HRID 1271427 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17].N1CCCCC1.C(=O)=O.Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:15][C:16]([OH:18])=[O:17])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehyde

Product 1

HCID 27375833-[4-fluoro-2-(trifluoromethyl)phenyl]prop-2-enoic AcidYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-Fluoro-2-trifluoromethyl-benzaldehyde (2 g, 10.2 mmol), malonic acid (1.2 g, 11.2 mmol), piperidine (0.087 g, 1 mmol) and pyridine (7 ml) was kept at reflux temperature until carbon dioxide formation ceased (3 h). After cooling to room temperature the reaction mixture was poured onto 40 g ice and 20 ml 6N HCl. The precipitate was isolated, washed with water and dried yielding 1.16 g (49%) 3-(4-fluoro-2-trifluoromethyl-phenyl)-acrylic acid.

Workup

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

Sources & evidence

ORD record
ord-cfc43d38416345dd9e55146ed08ca7dc
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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