Hydrochloric Acid → 2-(3-Fluorophenoxy)propanoic acid

Temperature

80 °C

To a solution of m-fluorophenol (24.2 g, 0.22 mol) in 79.2 ml of 25% aqueous sodium hydroxide heated to 45° C. with an oil bath was added 29.5 ml (0.26 mol) methyl 2-chloropropionate. The reaction mixture was heated to 80° C. for 17 hours and then allowed to cool. When the temperature reached about 40° C., concentrated HCl (25 ml) was added and the reaction mixture was allowed to cool to room temperature. The reaction mixture was extracted twice with 100 ml ethyl ether. The organic layers were combined and washed with 200 ml of 1.5M aqueous sodium carbonate. The aqueous layer was separated and acidified to pH 1, by pH test paper, by adding concentrated HCl. The acidified aqueous layer was extracted with 200 ml ethyl ether. The organic layer was separated, dried with MgSO4 and filtered. The solvent was removed in vacuo to yield 17 g (41% yield) of 2-(3' -fluorophenoxy)propionic acid as a yellow solid (m.p. 72.5°-74° C.).

1. temperatureto cool
2. customreached about 40° C.
3. temperatureto cool to room temperature
4. extractionThe reaction mixture was extracted twice with 100 ml ethyl ether
5. washwashed with 200 ml of 1.5M aqueous sodium carbonate
6. customThe aqueous layer was separated
7. additionby adding concentrated HCl
8. extractionThe acidified aqueous layer was extracted with 200 ml ethyl ether
9. customThe organic layer was separated
10. dry with materialdried with MgSO4
11. filtrationfiltered
12. customThe solvent was removed in vacuo

ORD record

ord-ebdd6c944da54f6aa8993277d53aafd6

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05502027