Water → Furan, 2-methyl-4-phenyl-

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.5 g HgSO4 in 30 mL of 2N HgSO4 was added 4.74 g (30 mmol) of 4,5-epoxy-4-phenyl-1-pentyne in 30 mL of absolute ethanol over a 5 minute period. The reaction mixture was refluxed for 0.25 hour and cooled to 23° C. After addition to 150 mL of H2O the mixture was extracted with hexanes three times. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Sublimination (90° C. at 15 mmHg) of the solid gave 3.6 g (76%) of 2-methyl-4-phenylfuran as a solid (m.p. 89°-91° C.) which was homogeneous by spectroscopic considerations; IR (KBr) 1599, 1545, 1440, 742 cm-1 ; 1HNMR (300 MHz, CDCl3) δ 7.62 (s, 1H), 7.50 (d, 2H, J=9.0 Hz), 7.38 (t, 2H, J=9.0 Hz), 7.28 (t, 1H, J=9.0 Hz), 6.33 (s, 1H), 2.35 (s, 3H).

Provenance & Evidence