Hydrochloric Acid → 3-Methyl-3-phenylbutanal

Participants

Reaction Conditions

Reaction Steps

A mixture of magnesium (4.48 g, 187 mmol), 1-chloro-2-methyl-2-phenylpropane (30.0 g, 179 mmol), a small amount of iodine and tetrahydrofuran (100 ml) was stirred at 70° C. for 2.5 hours. Then, the reaction mixture was cooled to 0° C., followed by adding dropwise thereto a solution of N-formylmorpholine (24.6 g, 214 mmol) in tetrahydrofuran (45 ml), and the resulting mixture was stirred at room temperature for 2 hours. Subsequently, the reaction mixture was re-cooled to 0° C. and 3N hydrochloric acid (180 ml) was added thereto, followed by stirring at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract solution was washed successively with an aqueous sodium thiosulfate solution, an aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography to obtain 18.0 g of 3,3-dimethyl-3-phenylpropionaldehyde.

Provenance & Evidence