Malonic Acid → 3-(3-Fluoro-4-methoxyphenyl)propionic acid

Temperature

120 °C

Malonic acid (7.5 g, 72.1 mmols) and piperidine (0.84 g, 9.83 mmols) were added to a pyridine (20 ml) solution of 3-fluoro-4-methoxybenzaldehyde (10.1 g, 65.5 mmols), and the mixture was stirred under heat at 120° C. for 7 hours. The reaction mixture was poured into water containing ice, and the powder that precipitated was taken out through filtration. The powder was dried and dissolved in acetic acid (300 ml) without being further purified. To this was added 5% palladium-carbon (3 g, containing 50% water), and the mixture was stirred in a hydrogen atmosphere at room temperature for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 8.54 g (yield: 66%) of the target compound.

1. additioncontaining ice
2. customthe powder that precipitated
3. filtrationwas taken out through filtration
4. customThe powder was dried
5. dissolutiondissolved in acetic acid (300 ml)
6. additionTo this was added 5% palladium-carbon (3 g, containing 50% water)
7. stirringthe mixture was stirred in a hydrogen atmosphere at room temperature for 2 hours
8. filtrationThe reaction mixture was filtered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-3f56aee3fe8c4366b34aa5eca4314da5

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06218429B1