Methanol → HCID 178458877, compound

Participants

Reaction Steps

A solution of 21 g (0.060 mol) of 2-propionyl-3-hydroxy-5-(4-benzyloxyphenyl)cyclohex-2-en-1-one in 250 mL of ethyl acetate and 250 mL of absolute ethanol was treated with 12 mL (0.12 mol) of cyclohexene and 0.7 g of 20 percent palladium hydroxide on carbon (Pearlman's catalyst) and the mixture was heated at reflux for 5 hours. The reaction mixture was cooled slightly and filtered through diatomaceous earth. Evaporation of the filtrate from the mixture gave a crude solid residue. Recrystallization of the residue from a 1:1 ethyl acetate-hexane mixture gave the above named product as a beige crystalline solid in a yield of 13.7 g (88 percent of theoretical). The product melted at 135°-137° C. Rf -0.45 (silica gel, 10:90 MeOH:CHCl3), 1H NMR (CDCl3): δ 1.13 (t, 3H, --CH3), 2.55-3.50 (m, 7H, ring protons and --CH2CH3), 6.60-7.12 (m, 5H, ArH's and ArOH), 18.15 broad s, 1H, enol H).

Provenance & Evidence