2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone → Cyclovalone

Participants

Reaction Steps

2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone (38j, 0.49 g, 1.1 mmol) was dissolved in methanol (100 ml) and stirred for 15 min at room temperature. Concentrated hydrochloric acid (3 drops) was added and the mixture stirred for 3 hr at 60° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.26 g (66%) of a yellow solid: mp 177-178° C. [expected mp 179-181° C.]; 1H NMR: δ 1.79 (m, 2H), 2.90 (t, 4H, J=5.4 Hz), 3.89 (s, 6H), 5.88 (s, 2H), 6.91 (s, 2H), 6.96 (d, 2H, J=4.8 Hz), 7.06 (d, 2H, J=8.0 Hz), 7.72 (s, 2H); 13C NMR: δ 23.1, 28.5, 56.0, 113.2, 114.4, 124.4, 128.5, 134.2, 136.9, 146.2, 146.4, 172.8.

Provenance & Evidence