Isophorone → HCID 54032451, compound

Participants

Reaction Steps

To a 5-liter flask equipped with a quartz immersion well and nitrogen bubbler was added, under nitrogen, 138 g. (1.0 mol.) of isophorone and 420 g. of freshly distilled cyclooctene. The flask was filled with dichloromethane and was bubbled with nitrogen for 1 hour. The solution was irradiated for 18.5 hours with an Hanovia 450 watt medium pressure mercury arc through a Corning 9700 glass filter. After 7 hours, an additional 82 g. of cyclooctene was added. The solution was concentrated in vacuo to obtain an oil which was distilled through a 45 cm. Vigreux-column to yield 218.4 g. (0.881 mol., 88% yield) of product, b.p. 106°-110° C./0.3 mm.Hg. The product by glpc consisted of 3 isomers in the approximate ratio of 75:12.5:12.5. IR: 1692 cm-1 confirmed the production of the desired product.

Provenance & Evidence