Organic Syntheses, CV 5, 585
Submitted by John M. Patterson
1
Checked by Melvin S. Newman and Herbert Boden.
1. Procedure
A mixture of
105.6 g. (1.1 moles) of freshly distilled furfural,
87.0 g. (1.0 mole) of 98% cyanoacetic acid (Note
1),
3.0 g. of ammonium acetate,
200 ml. of toluene, and
110 ml. of pyridine is placed in a
1-l. round-bottomed flask equipped with a
Stark and Dean water trap and
reflux condenser. The mixture is boiled under reflux for 2 days. The theoretical quantity of water is collected in the trap within 1 hour. Upon completion of the reflux period, the solvent is removed under reduced pressure by heating on a
water bath. The residue, distilled through a
15-cm. Vigreux column at 11 mm. pressure, yields
88.6–93.3 g. (
74.5–78%) of colorless liquid boiling at
95–97°,
n25D 1.5823–1.5825.
2. Notes
1.
Cyanoacetic acid was obtained from Distillation Products Industries, Rochester, New York, and used without further purification.
3. Discussion
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