Potassium Hydroxide → 5-Fluoro-2-(hydroxymethyl)benzoic acid

To a solution of 6-fluoroisobenzofuran-1(3H)-one (0.549 g, 3.61 mmol) in methanol (12 mL) and water (3 mL) at room temperature was added potassium hydroxide (0.350 g, 6.24 mmol). The mixture was heated at reflux for 1.5 hr. The mixture was concentrated under vacuum to a volume of about 3 mL. The residue was acidified with 1 M KHSO4 solution to pH 3-4. The insoluble material (inorganic salt) was removed by suction filtration and the filtrate was extracted with ethyl acetate (5×30 mL). The combined extract was dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.479 g, 2.82 mmol, 78% yield) as a white solid.

1. temperatureThe mixture was heated
2. temperatureat reflux for 1.5 hr
3. concentrationThe mixture was concentrated under vacuum to a volume of about 3 mL
4. customThe insoluble material (inorganic salt) was removed by suction filtration
5. extractionthe filtrate was extracted with ethyl acetate (5×30 mL)
6. extractionThe combined extract
7. dry with materialwas dried over anhydrous MgSO4
8. customRemoval of solvent under vacuum

ORD record

ord-4df4b53bdf68467399ee83b93425dd48

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685969B2