4,4'-Dimethoxybenzophenone → 3,3-bis(4-Methoxyphenyl)-2-propenal

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Reaction Steps

The compound was prepared according to the procedure described in Example 84 except that the reaction time was extended to 68 hours. The following reagents were used: 4,4'-dimethoxybenzophenone (24.2 g), diisopropylamine (32.2 mL) 1.55M n-butyl lithium in hexane (148 mL). acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofurane (200 mL). The usual work up furnished 25.6 g of an orange oil which was crystallized from ether-hexane to give 22.7 g of 3,3-bis(4-dimethoxyphenyl)-2-propenal, as a yellow solid, mp 55°-57° C. The analytical specimen, mp 56°-57° C., crystallized from the same solvent system had been prepared in a previous experiment. Anal. Calculated for C17H16O3 : C, 76.10; H. 6.01 Found: C, 76.29: H, 6.29.

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