1,3-Dihydroisobenzofuran → Phthalaldehyde

Participants

Reaction Conditions

Reaction Steps

To a mixture of 10 mmol of phthalan (isocoumaran), 1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile was introduced 10 mmol of nitrogenmonoxide, and the resultantmixture was stirred at 60° C. for 8 hours. Isolation of products in the reaction mixture by column chromatography on a silica gel revealed that phthalan was converted, at a rate of 15%, into phthalaldehyde (yield: 1%), 1-hydroxyphthalan (yield: 3%), NHPI adduct (yield: 3%), and an acetamide compound (yield: 3%).

Provenance & Evidence