Malonic Acid → 3-(2,3,5-trifluorophenyl)prop-2-enoic Acid

HRID 1929612Notes

Reaction equation

HRID 1929612 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>>[F:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[CH:4]=[CH:13][C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 27769502,3,5-Trifluorobenzaldehyde

Product 1

HCID 27770933-(2,3,5-trifluorophenyl)prop-2-enoic Acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3h20) between 2,3,5-trifluorobenzaldehyde (9.730 g; 60.777 mmol) and malonic acid (12.016 g; 115.477 mmol) gave the product 3-(2,3,5-trifluoro-phenyl)-acrylic acid as a colorless solid (8.310 g; 68%). LC-MS: tR=0.84 min.; [M+H]+: no ionisation.

Sources & evidence

ORD record
ord-cb6e11ce513b4791b586b7984c837820
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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