Formic Acid → 2,3-Dihydroxy-5-(perfluorohexyl)bicyclo[2.2.1]heptane

Participants

Reaction Steps

8.2 g (20 mmol) of the Diels-Alder reaction product of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octene (perfluorohexylethene) and cyclopentadiene are mixed with 20 ml of formic acid, 1.3 ml of 70 percent strength hydrogen peroxide (30 mmol) is added at 60° C., and the mixture is held at 60° C. for 36 hours. The low-boiling components are distilled off in vacuo. The residue is extracted with three portions (130 ml in total) of methylene chloride. The combined extracts are dried with magnesium sulfate and the methylene chloride is removed in vacuo. The residue is sublimed at 95° C. in an oil pump vacuum.

Provenance & Evidence