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An Advanced Laboratory Manual of Organic Chemistry by Michael Heidelberger

By Michael Heidelberger

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Am. Chetn. Soc. 7 ing the addition of ammonia until the solution remains definitely alkaline to litmus after shaking and boiling". The mixture is boiled 5 minutes, making certain that the reaction remains alkaline, and is filtered hot through a large Buchner funnel which, with the suction flask, has previously been warmed to prevent cracking. The precipitate of iron hydroxides is washed with a little hot dilute ammonia solution and the filtrate concentrated in vacuo until the ammonium salt filtrate of the amino acid begins to separate owing to the salting-out action of the ammonium sulfate present.

Oxidation with Potassium Ferricyanide. 8 Another very convenient method which gives a homogeneous product in good yield involves the oxidation of ^-nitroso-o-cresol to the />-nitro derivative, as given by Borsche and Berkhout,8 except that almost quantitative yields are obtained in the cold instead of on boiling as recommended by these authors 15 g. of £-nitroso-0-cresol (p 16) are dissolved in a solution of 150 g. of sodium hydroxide and 150 g. of potassium ferricyanide in 3 liters of water, and allowed 1 a Hirsch, Ber 18, 1512 (1885) Neville and Winther, Ber 15, 2978 (1882) 'Borsche and Berkhout, Ann 330, 95 (1904).

A stream of hydrobromic acid, which may be conveniently generated by dropping bromine on naphthalene and passing the vapors through several bottles containing naphthalene, is then passed m until the liquid is saturated, after which it is boiled under a reflux condenser for one hour, the reaction being: CH 2 : CHCH a OH + HBr > CH a :CHCH B Br + H 2 O. Under the conditions given very little addition of hydrobromic acid takes place at the double bond, although this would undoubtedly occur on long standing of the saturated solution in the cold.

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