Oxalic Acid → 3-Fluoro-2-methylphenol

Participants

Reaction Conditions

Reaction Steps

The 5.0 g (23.78 mmol) of 2-(3-fluoro-2-methylphenoxy)tetrahydro-2H-pyran was dissolved in 120 mL of methanol followed by addition of 3.21 g (35.67 mmol) of oxalic acid. The mixture was heat to 60° C. for 2 hours. The volatiles were removed in vacuo while maintaining a bath temperature of <29° C. to afford an oil, which was purified by silica gel chromatography with EtOAc/hexane (1:9). Concentration of the desired fractions afforded 2.19 g (73%) of a pale yellow oil, which later solidified upon standing: 1H NMR(CDCl3/400 MHz) 2.16 (d, 3H, J=2.0 Hz), 5.17 (s, 1H), 6.57 (d, 1H, J=8.4 Hz), 6.64 (t, 1H, J=8.8 hz), 7.00 (dd, 1H, J=8.4, 14.8 Hz); HRMS (EI+) m/z calcd for (C7H7FO) 126.0481, found 126.0470.

Provenance & Evidence