Formaldehyde → 2-Hydroxy-5-methyl-3-(2-phenylpropan-2-yl)benzaldehyde

Participants

Reaction Steps

Into a 500 ml reactor thoroughly purged with nitrogen, 21.0 ml of an ether solution containing 63.1 mmol of ethylmagnesium bromide and 40 ml of THF were introduced. To the reactor, a solution containing 13.61 g (60.1 mmol) of 2-cumyl-4-methylphenol diluted with 20 ml of a THF was dropwise added at 0° C. over a period of 1 hour, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 30 minutes. Then, 220 ml of toluene was added, and the system was heated to 100° C. to distill off about 50 ml of a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to 24° C., 4.37 g (145.5 mmol) of paraformaldehyde and 12.0 ml (86.0 mmol) of triethylamine were added, followed by stirring at 90° C. for 1 hour. The reaction solution was allowed to cool to room temperature and then quenched with 42 ml of 18% hydrochloric acid. The organic layer was concentrated, and the resulting liquid was purified by silica gel column chromatography to obtain 14.13 g (yield: 92%) of 3-cumyl-5-methylsalicylaldehyde.

Provenance & Evidence