Acrylic Acid → 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Distilled furan (141.7 g, 2.08 mol) and triacetoxyborane (1.19 g, 6.63 mmol) were charged in a similar reactor as in Example 4, and the mixture was cooled to −5° C. To this mixed solution was added acrylic acid (30.4 g, 0.42 mol) and the mixture was stirred at an inner temperature of −5° C. for 22 hr. The resulting crystals were collected by filtration through a glass filter, washed with diisopropyl ether (60 ml) cooled to not more than 5° C. and dried under reduced pressure for 2 hr. to give 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid as colorless crystals (11.4 g, endo form:exo form=98:2, purity >99%, yield 43% based on acrylic acid).

Provenance & Evidence