ethyl 4-(4-fluorophenoxy)butanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under cooling (0° C.), sodium ethanolate (2.18 g, 32 mmol) was added to a mixture of 4-fluorophenol ([371-41-5], 3.00 g, 27 mmol), ethyl 4-chlorobutyrate ([3153-36-4], 4.84 g, 32 mmol) and ethanol (15 ml), and the reaction mixture was then refluxed overnight. The solvent was evaporated, the residue was taken up in ethyl ester and was washed with water. After drying (Na2SO4), the solvent was evaporated, and 4-(4-fluoro-phenoxy)-butyric acid ethyl ester was isolated from the residue by column chromatography (silica gel, ethyl acetate/heptane). 1H NMR (d6-DMSO): 1.29 (t, 3H), 2.11 (tt, 2H), 2.51 (t, 2H), 3.96 (t, 2H), 4.13 (q, 2H), 6.79-6.85 (m, 2H), 6.92-6.99 (m, 2H). the reaction mixture was then refluxed overnight The solvent was evaporated was washed with water After drying (Na2SO4) the solvent was evaporated