Malonic Acid → 3-(3-Fluoro-4-methoxyphenyl)prop-2-enoic acid

HRID 1929613Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[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]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

Reactant 2

HCID 867Malonic Acid

HCID 676963-Fluoro-p-anisaldehyde

Product 1

HCID 1018433-(3-Fluoro-4-methoxyphenyl)prop-2-enoic acid

Procedure

According to the previously described general procedure (GP1), Knoevenagel condensation (75° C.; 3 h) between 3-fluoro-4-methoxybenzaldehyde (6.080 g; 39.445 mmol) and malonic acid (7.798 g; 74.946 mmol) gave the product 3-(3-fluoro-4-methoxy-phenyl)-acrylic acid as a colorless solid (7.530 g; 97%). LC-MS: tR=0.86 min.; [M+H]+: no ionisation.

Sources & evidence

ORD record: ord-e535183ed8294939a23738b8989ce18e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188082B2

Reaction notes

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