Formaldehyde → 3-Tert-butyl-2-hydroxy-5-methylbenzaldehyde

Participants

Reaction Steps

Into a 1 liter reactor thoroughly dried and purged with nitrogen, 9.68 g (58.93 mmol) of 2-tert-butyl-4-methylphenol and 100 ml of THF were introduced. To the reactor, 23.00 ml of an ether solution containing 69.00 mmol of ethylmagnesium bromide 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, 100 ml of toluene was added, and the system was heated to 95° C. to distill off a mixed solution of ether and THF, whereby an opaque white slurry was obtained. After the slurry was cooled to room temperature, 100 ml of toluene, 4.50 g (149.90 mmol) of paraformaldehyde and 12.50 ml (89.93 mmol) of triethylamine were added, followed by stirring at 95° C. for 2 hours. The reaction solution was allowed to cool to room temperature and then quenched with 300 ml of 1N hydrochloric acid. The organic layer was concentrated and purified by a silica gel column to obtain 7.36 g (yield: 65%) of 3-t-butyl-5-methylsalicylaldehyde.

Provenance & Evidence