Ethyl 4,4-dibutyl-1-hydroxy-3-oxo-3,4-dihydro-2-naphthalenecarboxylate → 1,1-dibutyl-4-hydroxy-2(1H)-naphthalenone

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Reaction Conditions

Reaction Steps

A solution of the product of Example 4F (200 mg, 0.58 mmol) in dioxane (3 mL) and 10% HCl solution (10 mL) was stirred at 100° C. for 5 hours, cooled to 25° C. and extracted with dichloromethane (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was recrystallized from hexanes to give the title compound (140 mg, 88%). 1H NMR (300 MHz, DMSO-d6): δ 11.72, 11.46 (s, 1 H), 7.92 (m, 1 H), 7.61 (m, 1 H), 7.37 (m, 2 H), 5.81, 5.64 (two s, 1 H), 1.99 (m, 4 H), 1.05 (m, 4 H), 0.82 (m, 2 H), 0.67 (t, J=6.99 Hz, 6 H), 0.44 (m, 2 H).

Provenance & Evidence