Organic 2 Review Problem 263

Organic 2 Review Problem 263 - PREPARATIONS 247 separates,...

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PREPARATIONS 247 separates, the reaction being complete after about 5 minutes' shaking. Filter the ester at the pump, wash with dilute sodium hydroxide solution, then thoroughly with water, and drain. Recrystallise from methylated spirit, allowing the hot solution to cool slowly at first: finally cool in ice-water. The benzyl p -nitrobenzoate separates in colourless crystals, m.p. 84°. Yield, r6 g. Methyl 3,5-Dinitrobenzoate. (NO 2 ) 2 C 6 H 3 COOCH 3 . (Semi-micro Scale.) The reaction between 3,5-dinitrobenzoyl chloride and compounds containing the OH, NH 2 , or NH groups is very rapid, and therefore is particularly suitable for identification purposes (cf. pp. 335, 338, 381). It is usual to have sodium hydroxide present during the reaction with phenols and amino-acids, but this is not necessary with alcohols if they are dry. Required: 3,5-Dinitrobenzoyl chloride, i g.; methanol, 2-5 ml. Place i g. of powdered 3,5-dinitrobenzoyl chloride in a small conical
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