Sulfuric Acid → 6-(4-Chlorophenyl)-4-hydroxy-2H-pyran-2-one

Participants

Reaction Steps

The title compound (1.56 g, m.p. 247°-249° C.) was prepared in a similar manner as that demonstrated in the preparation of Example N using the following: 60% NaH (0.904 g, 22.6 mmol), THF (50 mL), ethyl acetoacetate (3.00 g, 22.6 mmol), lithium diisopropylamine in THF (39.8 mL, 24 mmol), 4-chloro-N-methoxy-N-methylbenzamide (3.73 g, 22.6 mmol), 90% H2SO4 (20 mL). H NMR (300 MHz, DMSO-d6) δ 11.950 (bs, 1 H), 7.878 (d, 1 H, J=9 Hz), 7.584 (d, 1 H, J=9 Hz), 6.812 (d, 1 H, J=2 Hz), 5.409 (d, 1 H, J=2 Hz).

Provenance & Evidence