Typical Procedure for 3-Phenylpropanenitrile 3a

80 mmol) in glyme (10 ml) is added dropwise to the nickel (12.3 mmol) in refluxing glyme for 30 min. After additional heating is continued for 15 min, the mixture is cooled and poured into a separatory funnel containing 3% hydrochloric acid (100 ml) and is extracted with chloroform (2xKX)ml). 

The aqueous phase is extracted with chloroform (lx 150ml), and the combined extracts are washed with water (200 ml), dried with anhydrous sodium sulfate, and concentrated. The residual oil is chromatographed on silica gel, eluting with chloroform to give 3a yield 0.732 g (57%) (Table 7.5). 

4 Reformatsky-Type Additions of Haloacetonitriles to Aldehydes Mediated by Metallic Nickei 

Isolated by silica gel chromatography upon elution with chloroform. 

5 Preparation of Symmetrical 1,3-Diarylpropan-2-ones from Benzylic Halides and Alkyl Oxalyl Chlorides 

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