1-Butanol → Dibutyl squarate

Participants

Reaction Steps

Protected by a nitrogen atmosphere, a mixture of 1-butanol (64 mL), toluene (42 mL), and 1,2-dihydroxy-1-cyclobutene-3,4-dione (21.43 g, 0.1878 mole) was heated under reflux with stirring under a Dean-Stark water separator until water stopped passing over (7.6 mL of water was collected). Reflux was continued for a further 30 minutes, then the excess toluene and butanol were distilled off under reduced pressure (50-100 mm Hg) to give the title compound as a yellow liquid. The concentrate was diluted with 25 mL of methanol.

Provenance & Evidence