Ethanol → Ethyl 2-(4-fluorophenyl)-2-hydroxyacetate

To a cooled solution of 2-(4-fluorophenyl)-2-hydroxyacetic acid (5.0 g, 29.4 mmol) in ethanol was added con. H2SO4 (10 mL) over a period of 10 min. The reaction mixture was heated at reflux for 5 h. The solvent was evaporated under reduced pressure and the residue was diluted with ethyl acetate (25 mL). The organic solution was washed with aqueous saturated NaHCO3 (25 mL×2), water (20 mL), brine solution (10 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give ethyl 2-(4-fluorophenyl)-2-hydroxyacetate (5.0 g, 90%) as crude compound (oily liquid). The crude compound was taken to the next step without further purification. LC-MS (M+H2O)+=216. 1H NMR (400 MHz, DMSO-d6): δ 7.43-7.46 (2H, m), 7.17-7.20 (2H, m), 6.11-6.13 (1H, m), 5.14 (1H, d, J=5.20 Hz), 3.35-4.13 (2H, m), 1.12-1.15 (3H, m).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 5 h
3. customThe solvent was evaporated under reduced pressure
4. additionthe residue was diluted with ethyl acetate (25 mL)
5. washThe organic solution was washed with aqueous saturated NaHCO3 (25 mL×2), water (20 mL), brine solution (10 mL)
6. dry with materialdried over anhydrous Na2SO4
7. customevaporated under reduced pressure

ORD record

ord-cd3a0c97372f4cb1a1e0953ab99eedac

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486952B2