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

HRID 1929607Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=O.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:15][C:16]([OH:18])=[O:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11]

Participants

Reactant 2

HCID 867Malonic Acid

HCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 27375813-[3-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoic Acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3h20) between 3-fluoro-4-trifluoromethyl-benzaldehyde (9.000 g; 46.848 mmol) and malonic acid (9.262 g; 89.012 mmol) gave the product 3-(3-fluoro-4-trifluoromethyl-phenyl)-acrylic acid as a colorless solid (9.520 g; 87%). LC-MS: tR=0.90 min; [M+H]+: no ionisation.

Sources & evidence

ORD record: ord-dfcc2b13d23c4018bb76a150a67fa1f0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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