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

HRID 1929606Notes

Reaction equation

HRID 1929606 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:15][C:16]([OH:18])=[O:17]>>[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:15][C:16]([OH:18])=[O:17]

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 27834023-[2-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoic Acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3h20) between 2-fluoro-4-(trifluoromethyl)benzaldehyde (5.000 g; 26.027 mmol) and malonic acid (5.145 g; 49.451 mmol) gave the product 3-(2-fluoro-4-trifluoromethyl-phenyl)-acrylic acid as a colorless solid (5.030 g; 82.5%). LC-MS: tR=0.89 min; [M+H]+: no ionisation.

Sources & evidence

ORD record
ord-88633a0df75f438cb4b4eee17b68db9e
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

Loading…