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The mixture was then refluxed with a calcium chloride drying tube for ten minutes and left to cool for an hour taking on a dark almost black colour. The reaction mixture was then poured onto ice (60 mL) and stirred to form brown mixture with some greenish black precipitate. Aqueous sodium hydroxide (37.5 mL, 3M) was added to the mixture and solid sodium bicarbonate was added until the mixture was neutralised. The mixture was left to stand for an hour with stirring before the crude product was collected with vacuum filtration.The product was air dried for a couple of minutes then boiled with hexane (20 mL) leaving behind a brown- black gummy substance...
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