Formaldehyde → 3-t-butyl-5-methoxysalicylaldehyde

Participants

Reaction Steps

Into a 1 liter reactor thoroughly dried and purged with argon, 36.6 ml of an ether solution containing 110 mmol of ethylmagnesium bromide and 73.4 ml of ether were introduced. To the reactor, a solution containing 18.39 g (100 mmol) of 2-tert-butyl-4-methoxyphenol diluted with 90 ml of a THF was dropwise added at 0° C. over a period of 30 minutes, then the temperature of the system was slowly raised to room temperature, and the reaction solution was stirred at room temperature for 1 hour. Then, 350 ml of toluene was added, and the system was heated to 100° C. to distill off about 180 ml of a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to 50° C., 4.50 g (150 mmol) of paraformaldehyde and 21.0 ml (150 mmol) of triethylamine were added, followed by stirring at 80 to 90° C. for 1.5 hours. The reaction solution was allowed to cool to room temperature and then quenched with 10% hydrochloric acid. The organic layer was concentrated, and the solid precipitated was vacuum dried to obtain 11.66 g (yield: 56%) of 3-t-butyl-5-methoxysalicylaldehyde.

Provenance & Evidence