Malonic Acid → 3-(2,4-Difluoro-3-methyl-phenyl)-acrylic acid

Reaction equation

[F:1][C:2]1[C:9]([CH3:10])=[C:8]([F:11])[CH:7]=[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]([CH3:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:13][C:14]([OH:16])=[O:15]

Participants

Reactant 2

HCID 867Malonic Acid

HCID 121374892,4-Difluoro-3-methylbenzaldehyde

Product 1

HCID 667339963-(2,4-Difluoro-3-methyl-phenyl)-acrylic acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3h30) between 2,4-difluoro-3-methyl-benzaldehyde (1.560 g; 9.744 mmol) and malonic acid (1.926 g; 18.515 mmol) gave the product 3-(2,4-difluoro-3-methyl-phenyl)-acrylic acid as a pale yellow solid (1.600 g; 83%). LC-MS: tR=0.86 min; [M+H]+: no ionisation.

Sources & evidence

ORD record: ord-df10f7ca732c48608ccd88a057c12193
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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