Formaldehyde → 3-tert-Butyl-2-hydroxybenzaldehyde

Participants

Reaction Steps

Into a 500 ml reactor thoroughly dried and purged with argon, 7.51 g (50 mmol) of 2-tert-butylphenol and 54 ml of THF were introduced. To the reactor, 18.53 ml of an ether solution containing 55.6 mmol of ethylmagnesium bromide was dropwise added at 0° C., 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, 180 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 room temperature, 3.75 g (125 mmol) of paraformaldehyde and 10.45 ml (75 mmol) of triethylamine were added, followed by stirring at 88° C. for 1 hour. The reaction solution was allowed to cool to room temperature and then quenched with 10% hydrochloric acid. The organic layer was concentrated and purified by a silica gel column to obtain 6.22 g (yield: 70%) of 3-t-butylsalicylaldehyde.

Provenance & Evidence