Hydrochloric Acid → 4-(2-Fluoroethoxy)benzoic acid

Temperature

65 °C

To a stirred solution of 50% w/v KOH (1.3 ml) and 4-(2-fluoroethoxy)benzaldehyde (0.5 g, 2.98 mmol) in MeOH (6 ml) at 65° C. was added dropwise over 20 min aqueous hydrogen peroxide (30 wt. % in water, 2.45 ml). On completion of the addition the reaction mixture was heated at 65° C. for a further 10 min. On cooling to room temperature, the reaction mixture was acidified with 1 M HCl and extracted with Et2O (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried (Na2SO4) and the solvent removed under reduced pressure to give a solid which was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.278 g, 63%) as a colourless solid.

1. customat 65° C.
2. additionOn completion of the addition the reaction mixture
3. temperatureOn cooling to room temperature
4. extractionextracted with Et2O (3×30 ml)
5. washThe combined organic extracts were washed with brine (30 ml)
6. dry with materialdried (Na2SO4)
7. customthe solvent removed under reduced pressure
8. customto give a solid which
9. customwas purified by flash chromatography (1:1 Hexane/EtOAc)

ORD record

ord-db5125dd0639494b9ee21fc6a3c480e7

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895313B2