Of ethyl bromomalonate with itself

A mixture of 200 g. (1.9 moles) of anhydrous sodium carbonate (Note 1) and 300 g. (1.25 moles) of ethyl bromomalonate (Org. Syn. 7, 34) is heated for three hours in a i-l. flask (Note 2) immersed in an oil bath at 150-160° (Note 3). After the heating period, 300 cc. of xylene (Note 4) is added while the contents of the flask are still hot (Note 5). The solid is broken up carefully with a rod and the mixture is transferred to a 2-1. beaker. The reaction flask is then rinsed with a mixture of 100 cc. of xylene and 100 cc. of water. This washing is poured into the 2-1. beaker and an additional 600 cc. of water is added. The solid readily dissolves upon stirring. The liquid mixture is transferred to a separatory funnel, shaken well, and allowed to settle (Note 6). The lower aqueous layer is discarded (Note 7). The xylene layer is transferred to a i-l. distilling flask and distilled until the temperature of the liquid itself is 170°. The liquid residue is then transferred to a 500-cc. Claisen flask and distilled under reduced pressure. The forerun up to i7o°/r5 mm. is discarded. The product is collected at 170-23o°/i5 mm. (Notes 8 and 9). The distillate solidifies within about fifteen minutes. The yield is 150-160 g. (75-80 per cent of the theoretical amount). 

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