Acetic Acid → Methyl 4-(4-fluoro-3-methylphenyl)butanoate

Temperature

0 °C

The compound obtained in (1) above (172 gm) was dissolved into 700 ml of acetic acid. To the solution were added 10 ml of 40% perchloric acid and 30 gm of 10% palladium-on-carbon to effect catalytic hydrogenation under 6 atm. The catalyst was removed by filtration and acetic acid was evaporated. Upon the addition of 2 l of water, the residue was extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and 1 l of methanol was added to the residue. After cooling to 0° C., 269 gm of thionyl chloride was slowly dropped to the solution, followed by the addition of 10 ml of dimethylformamide. The mixture was stirred for 12 hours at room temperature, the reaction product was concentrated, and extracted with chloroform. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain 153 gm of the title compound.

1. customThe catalyst was removed by filtration and acetic acid
2. customwas evaporated
3. additionUpon the addition of 2 l of water
4. extractionthe residue was extracted with chloroform
5. washwashed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated
8. addition1 l of methanol was added to the residue
9. addition269 gm of thionyl chloride was slowly dropped to the solution
10. additionfollowed by the addition of 10 ml of dimethylformamide
11. concentrationthe reaction product was concentrated
12. extractionextracted with chloroform
13. washThe extract was washed with water and saturated brine
14. dry with materialdried over anhydrous magnesium sulfate
15. customThe solvent was evaporated

ORD record

ord-73ee5d387a36434d8695c6534c001f12

Source dataset

uspto-grants-1998_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05770605