Diethyl Ether → 2,2-Dimethyl-3-(3-phenyl-2-propenoxy)propionaldehyde

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Reaction Steps

In a dry three-neck flask equipped with a mechanical stirrer and an addition funnel was placed 128 g of pyridinium dichromate and 320 ml of dry CH2Cl2. The mixture was vigorously stirred and a solution of 32.37 g (0.147 mole) of 2,2-dimethyl-3-(3-phenyl-2-propenoxy)propanol, the product of Example 10a, in 50 ml of CH2Cl2 was added in one portion. The reaction mixture was stirred at room temperature for three days and then was poured into 400 ml of ethyl ether. The resulting mixture was filtered through a column packed with dry silica gel to obtain a yellow filtrate. The filtrate was concentrated to obtain a yellow residue. Kugelrohr distillation of the residue gave the title compound, bp 90°/0.05 mm Hg.

Provenance & Evidence