1,2,3,5-Tetrahydroxybenzene → HCID 85756659, compound

Participants

Reaction Steps

In a vessel fitted with a calcium chloride tube, 1.00 g (7.04 mmol) of 1,2,3,5-tetrahydroxybenzene (3) was dissolved in 20 ml of nitrobenzene and stirred. Into the stirred mixture, 2.82 g (21.1 mmol, 3.00 equivalents) of granular aluminum chloride was added piecemeal and stirred. One hour thereafter, a nitrobenzene (5.0 ml) solution of 0.750 g (7.04 mmol, 1.00 equivalent) of isobutyryl chloride was added dropwise. Ten hours thereafter, the reaction solution was poured into 100 ml of cold 2 M hydrochloric acid solution, stirred for 30 minutes, and then extracted from ether. The ether layer was washed with water, distilled to remove ether, combined with a large volume of water, and distilled water under reduced pressure to remove nitrobenzene by steam distillation. The residue was extracted from ether, washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 1.38 g of crude product. By purifying the crude product by column chromatography (SiO2, 20 g of Wako Gel C-300, hexane:ether=1:1), 441 mg (yield 65.9%) of the product (8) was obtained in the form of yellow powder crystals.

Provenance & Evidence