The procedure has been optimized for the preparation of 2,5-Dimethoxynitrostyrene, and the yield is typically very high for this product, usually
exceeding 95%
2,5-Dimethoxybenzaldehyde (83.1g, 500 mmol) and ethylenediammonium diacetate (9.0g, 50 mmol) was dissolved with stirring in 400ml isopropanol with
gentle heating until a clear solution was obtained. Nitromethane (36.6g, 600 mmol) was then added, and during the next hour the solution turned a deep
orange, and stirring was discontinued. The solution was then allowed to stand at room temp for 36h, and the orange crystalline mass was broken up with
a large spatula and was filtered with suction until no more liquid came through. The crystals was then washed with 100ml cold isopropanol in the
buchner funnel, and sucked as dry as possible. After air drying overnight, the crispy and intensely orange 2,5-dimethoxynitrostyrene weighed 100.5g
(480 mmol, 96%). |