1,2,3,5-Tetrahydroxybenzene → HCID 14446594, compound

Participants

Reaction Steps

Under an atmosphere of argon, 4.28 g (30.14 mmol) of 1,2,3,5-tetrahydroxybenzene (3) was dissolved by stirring in 70 ml of nitrobenzene. The solution was cooled with water. To the cold solution, 16.1 g (120.56 mmol, 4.00 equivalents) of granular aluminum chloride was added piecemeal and stirred. To the stirred mixture, 3.67 ml (30.1 mmol, 1.00 equivalent) of isovaleryl chloride was added dropwise. After 5 hours, the reaction solution was poured into 100 ml of a cold.2 M hydrochloric acid solution, stirred for 20 minutes, and extracted from ether. The organic layer was washed with water, distilled to remove ether, combined with a large volume of water, and distilled under reduced pressure to remove nitrobenzene. The residue was extracted from ether, washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to obtain a crude reaction product. By purifying the crude product by silica gel column chromatography (300 g of Wako Gel C-200, hexane:ethyl acetate=2:1), 1.85 g (yield 27.2%) of the product (9) was obtained in the form of yellow powder crystals.

Provenance & Evidence