3-Nitrophthalio anhydride

For alcohols of b.p. below 150, mix 0-5 g. of 3-nitrophthalio anhydride (Section VII,19) and 0-5 ml. (0-4 g.) of the dry alcohol in a test-tube fitted with a short condenser, and heat under reflux for 10 minutes after the mixture liquefies. For alcohols boiling above 150°, use the same quantities of reactants, add 5 ml. of dry toluene, heat imder reflux until all the anhydride has dissolved and then for 20 minutes more remove the toluene under reduced pressure (suction with water pump). The reaction product usually solidifies upon cooling, particularly upon rubbing with a glass rod and standing. If it does not crystallise, extract it with dilute sodium bicarbonate solution, wash the extract with ether, and acidify. EecrystaUise from hot water, or from 30 to 40 per cent, ethanol or from toluene. It may be noted that the m.p. of 3-nitrophthalic acid is 218. ... 

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