Ethyl 4-hydroxycrotonate (CAS NO.: ), with other names like , 4-hydroxy-, ethyl ester, (E)-, could be produced through the following synthetic methods.

A dry, 2-L, one-necked, round-bottomed flask is equipped with a 1-L pressure-equalizing funnel and a large magnetic stirring bar. The system is flame-dried under an internal atmosphere of dry nitrogen. The flask is charged with 300 mL of anhydrous tetrahydrofuran and 100 g of monoethyl fumarate. The solution is then stirred under nitrogen and brought to about -5°C using an ice–salt/methanol bath (-10°C). A 1 M solution of 700 mL (0.70 mol) of borane–tetrahydrofuran complex is cautiously added dropwise (rapid H2 evolution occurs) with rigorous temperature control to avoid an exothermic reaction. The ice–salt bath is maintained in position throughout the 90 min of addition. The stirred reaction mixture is then gradually allowed to warm to room temperature over the next 8–10 hr. The reaction is carefully quenched at room temperature by dropwise addition of 1 : 1 water : acetic acid (ca. 20 mL) with stirring until no more gas evolution occurs. The reaction is concentrated at room temperature and water pump pressure to a slurry by removal of most of the tetrahydrofuran. The slurry is carefully poured over a 20-min period into 300 mL of ice-cold, saturated sodium bicarbonate solution with mechanical stirring to avoid precipitation of solids, and the product is extracted with 300 mL of ethyl acetate. The aqueous layer is again extracted with 100 mL of ethyl acetate. The organic layers are combined, washed once with 200 mL of saturated sodium bicarbonate, then dried well with anhydrous magnesium sulfate.

Solvent removal at reduced pressure gives 61 g (67% yield) of essentially pure ethyl hydroxycrotonate.

An analytical sample may be prepared by quick distillation (or Kugelrohr distillation) at 117–120°C (15 mm), but there is significant loss of material because of decomposition in the distillation pot. From 1 g of product, 0.72 g of pure material is obtained in this way, and recovery decreases as scale of distillation increases.