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

Participants

Reaction Conditions

Reaction Steps

Into a 1 liter reactor thoroughly purged with nitrogen, 43.5 ml of an ether solution containing 130.7 mmol of ethylmagnesium bromide and 70 ml of THF were introduced. To the reactor, a solution containing 30.16 g (124.5 mmol) of 2-cumyl-4-methoxyphenol diluted with 80 ml of a THF was dropwise added at 0° C. over a period of 30 minutes. Then, 500 ml of toluene was added, and the system was heated to 100° C. to distill off about 40 ml of a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to 15° C., 9.04 g (301.3 mmol) of paraformaldehyde and 24.8 ml (178.0 mmol) of triethylamine were added, followed by stirring at 90° C. for 15 minutes. The reaction solution was allowed to cool to room temperature and then quenched with 84 ml of 18% hydrochloric acid. The organic layer was washed with 400 ml of water, 200 ml of a sodium hydrogencarbonate aqueous solution and a sodium chloride aqueous solution (200 ml×2), and then concentrated. The resulting liquid was purified by silica gel column chromatography to obtain 27.27 g (yield: 81%) of 3-cumyl-5-methoxysalicylaldehyde.

Provenance & Evidence