Water → HCID 14128060, compound

Participants

Reaction Steps

A portion (4.5 g) of the 5-chloro-3-(2-chlorophenyl)7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-methanol prepared in Example 13 was dissolved in 200 ml of acetone. To the stirred solution, a mixture of chromium (VI) oxide (4.9 g), water (10 ml) and concentrated sulfuric acid (6.9 g) was added dropwise over time, and the resulting mixture was stirred for 8 hours at room temperature. The insolubles were filtered off by suction. After distilling off the acetone, water was added to the residue and the solution was subjected to extraction with ether. The ether layer was washed with water and dried. After distilling off the solvent, the residue was recrystallized from acetone-water, yielding 2.6 g of 5-chloro-3-(2-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 220°-221.5° C. This compound exhibited a mass spectrum having a molecular ion peak at m/e 349.

Provenance & Evidence