Malonic Acid → 3-(3-Fluorophenyl)-2-propenoic acid

HRID 1844044Notes

Reaction equation

HRID 1844044 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 680093-Fluorobenzaldehyde

Product 1

HCID 886063-(3-Fluorophenyl)-2-propenoic acidYield 98.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Fluorobenzaldehyde (5 g, 40.28 mmol) in pyridine (50 mL) was reacted with malonic acid (5.4 g, 52.3 mmol) and piperidine (343 mg, 4.0 mmol) at 75° C. for 12 hours to afford 6.6 g (96.9%) of the crude product which was used in the next step without further purification.

Sources & evidence

ORD record
ord-de2d629f75cb4adfa9a8ac5f926313b4
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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