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Maleic anhydride (100.0 g, 1.02 mole) was dissolved in anhydrous ethanol (60 ml, excess) by heating the mixture in an erlenmeyer flask on a steam bath. Thionyl chloride (1.0 ml) was added using a syringe and the mixture heated with stirring for ten minutes. To the turbid mixture was added carbon tetrachloride (100 ml) and the liquid quickly filtered through a Buchner funnel having a coarse glass frit. The solid was discarded. The filtrate was allowed to cool during which the time the ethyl hydrogen fumarate product (92 g, 63%) crystallized.

1. temperatureby heating the mixture in an erlenmeyer flask on a steam bath
2. temperaturethe mixture heated
3. filtrationthe liquid quickly filtered through a Buchner funnel
4. temperatureto cool during which the time the ethyl hydrogen fumarate product (92 g, 63%)
5. customcrystallized