1-Butanol → Butanedioic acid, 2-hydroxy-, 1,4-dibutyl ester

Participants

Reaction Conditions

Reaction Steps

A 100 mL three-neck flask, equipped with a magnetic stir bar, a Claisen adapter with a thermocouple and a nitrogen inlet, and a short path condenser, was charged with 4.45 grams of dimethyl malate, 40 mL 1-butanol, and 0.51 gram of p-toluenesulfonic acid. The reaction was stirred at 115° C. for 3.7 hours with a nitrogen sweep. The reaction mixture was taken up in ethyl acetate, extracted with dilute aqueous sodium bicarbonate, washed three times with water, dried over magnesium sulfate, and filtered. Solvent was removed by rotary evaporation to yield 6.8 grams of a straw-colored liquid.

Provenance & Evidence