Malonic Acid → 3-(3,4,5-Trifluorophenyl)-2-propenoic acid

HRID 1929610Notes

Reaction equation

HRID 1929610 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH:5]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:13][C:14]([OH:16])=[O:15])[CH:7]=[C:8]([F:11])[C:9]=1[F:10]

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 27771023-(3,4,5-Trifluorophenyl)-2-propenoic acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3 h) between 3,4,5-trifluorobenzaldehyde (7.000 g; 43.724 mmol) and malonic acid (8.644 g; 83.076 mmol) gave the product 3-(3,4,5-trifluoro-phenyl)-acrylic acid as a yellow solid (8.600 g; 97%). LC-MS: tR=0.91 min.; [M+H]+: no ionisation.

Sources & evidence

ORD record
ord-d69d67d00315486fb0dae7c1a6de6efd
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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