Diethyl Ether → HCID 21477447, compound

Participants

Reaction Steps

Under a stream of argon, 1.30 g (9.15 mmol) of 1,2,3,5-tetrahydroxyphenol (3) was suspended in 13 ml of ether and 0.935 ml (9.15 mmol, 1.00 equivalent) of benzonitrile was added to the suspension with stirring. The resultant mixture was cooled with ice water and 0.624 g (4.57 mmol, 0.50 equivalent) of zinc chloride was added and they were stirred at room temperature for 6 hours by bubbling hydrogen chloride gas throughout. The aeration of the mixture with the gas was stopped and the mixture was left standing at 4° C. for 13 hours. From the tarry precipitates consequently formed was removed the ether layer by decantation. The precipitates were stirred in an ice bath and 39 ml of water was added and were then refluxed for 2 hours. The product of reflux was filtered while kept in hot and stand still to form red brown from the filtrate. By dissolving the crystals again in ether, filtering off insolubles from the solution, and concentrating, 0.97 g (yield 45.9%) of the product (10) was obtained in the form of orange powder crystals.

Provenance & Evidence