Formaldehyde → Benzoxazines

Participants

Reaction Steps

Hydroquinone (8.23 g, 75 mmol), allylamine (8.57 g, 150 mmol) and toluene (100 mL) were placed in a 250 mL flask. Paraformaldehyde (9.0 grams, equivalent to 300 mmole formaldehyde) was added along with a magnetic stir bar. The flask was equipped as described in Example 1 and brought to reflux. The full theoretical amount of water was collected within forty-five minutes of reflux. The toluene solution was washed with six 25 ml portions of 5% aqueous sodium hydroxide, and three 30 ml aliquots of water. The toluene solution was then dried over anhydrous magnesium sulfate and then passed over 26 grams of activated, neutral alumina. The toluene was removed to yield 11.0 grams (54% of theory) of a red, semi-solid material.

Provenance & Evidence