Potassium Hydroxide → 4-(3-Fluorophenyl)butanoic acid

Methyl-4-(3-fluorophenyl)-4-oxobutanoate (25.27 g), hydrazine hydrate (24.29 cm3) and potassium hydroxide pellets (20.50 g) were dissolved in ethylene glycol (150 cm3) and the mixture was heated at reflux for 1.25 h. The excess hydrazine hydrate was distilled off until the temperature at the still-head reached 160° C. The reaction mixture was then cooled, diluted with water (400 cm3) and the resultant aqueous mass was washed with diethyl ether (2×150 cm3) and then acidified with hydrochloric acid (5 M, 150 cm3). The acidic mixture was then extracted with diethyl ether (2×150 cm3) and the combined extracts were dried (Na2SO4) and the solvent was removed under reduced pressure to provide the title compound (15.51 g) as a dark oil.

1. temperaturethe mixture was heated
2. temperatureat reflux for 1.25 h
3. distillationThe excess hydrazine hydrate was distilled off until the temperature at the
4. customstill-head reached 160° C
5. temperatureThe reaction mixture was then cooled
6. additiondiluted with water (400 cm3)
7. washthe resultant aqueous mass was washed with diethyl ether (2×150 cm3)
8. extractionThe acidic mixture was then extracted with diethyl ether (2×150 cm3)
9. dry with materialthe combined extracts were dried (Na2SO4)
10. customthe solvent was removed under reduced pressure

ORD record

ord-049060d262294086a9936d5f227b46b2

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410592B1