Organic Syntheses, CV 1, 536
Submitted by C. S. Marvel and E. M. McColm.
Checked by H. T. Clarke and E. E. Dreger.
1. Procedure
In a
5-l. round-bottomed flask fitted with a stopper holding a
reflux condenser and a
separatory funnel are placed
294 g. (6 moles) of sodium cyanide and 300 cc. of water. The flask is heated on a
steam bath until most of the
sodium cyanide is in solution. This requires two to three hours. A solution of
500 g. (2.47 moles) of trimethylene bromide (Note
1) in
1 l. of 95 per cent alcohol is then added through the separatory funnel over a period of forty to sixty minutes. The mixture is refluxed for thirty to forty hours (Note
2) on a steam bath. Then the solvent is removed, preferably under reduced pressure, using an
oil bath.
2. Notes
1. Larger runs seem to give slightly lower yields.
2. The yield is lower if the heating is continued too long, owing to partial hydrolysis of the
cyanide.
3. Very little
ethyl acetate is lost in this procedure if it is distilled at ordinary pressures. If it is not entirely removed before the pressure is reduced, considerable foaming occurs.
3. Discussion
This preparation is referenced from:
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