Hydrochloric Acid → 4-(3-Fluorophenoxy)butanoic acid

温度

25 °C

A 1 L 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 17.17 g (150 mmol) of 3-fluorophenol, 33.82 g (165 mmol) of ethyl 4-bromobutyrate, 24.88 g, 180 mmol potassium carbonate and 600 mL of 2-butanone. The slurry heated to reflux. After stirring for 21 hr at reflux, the reaction mixture was cooled to 25° C., filtered and concentrated. The residue was taken up in of water and treated with 150 mL of 2N aqueous sodium hydroxide (300 mmol). The reaction mixture was heated to reflux for 30 min and cooled to 25° C. The brown solution was acidified with aqueous 150 ml of 2N hydrochloric acid. The resulting pink solid was isolated by filtration washing with hexanes to yield 25.04 g, mp 53-54° C. Combustion analysis: Found: C, 60.53; H, 5.79%; F, 9.84%; C10H11FO3 requires C, 60.60; H, 5.59%; F, 9.59%; 1H NMR (d6-DMSO): δ 12.1, bs, 1H (COOH); δ 7.20, dd, 1H, (H para to OR); δ 6.7, m, 3H (aryl H's); δ 3.90, t 2H, (CH2 α to O); δ 2.30, t, 2H (CH2 α to COOR); δ 1.87, p, 2H (CH2 β to ArO and COOH).

1. customA 1 L 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser
2. temperatureThe slurry heated to reflux
3. temperatureat reflux
4. filtrationfiltered
5. concentrationconcentrated
6. temperatureThe reaction mixture was heated
7. temperatureto reflux for 30 min
8. temperaturecooled to 25° C
9. customThe resulting pink solid was isolated by filtration
10. washwashing with hexanes
11. customto yield 25.04 g, mp 53-54° C

ORDレコード

ord-a034c42d4db94c54b90ff97dc1d4b828

出典データセット

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08895777B2