Org. Synth. 1960, 40, 46
DOI: 10.15227/orgsyn.040.0046
3-(2-FURYL)ACRYLONITRILE
[2-Furanacrylonitrile]
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
The method described is a modification of the procedure used by Ghosez
2 to synthesize
cinnamonitrile.
3-(2-Furyl)acrylonitrile has been prepared by catalytic condensation of
furfural with
acetonitrile in the vapor phase at 320°,
3 by dehydration of the corresponding amide over
phosphorus pentachloride,
4 and by decarboxylation of
3-(2-furyl)-2-cyanoacrylic acid.
5
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
ammonium acetate (631-61-8)
acetonitrile (75-05-8)
phosphorus pentachloride (10026-13-8)
pyridine (110-86-1)
toluene (108-88-3)
cyanoacetic acid (372-09-8)
Furfural (98-01-1)
3-(2-Furyl)acrylonitrile,
2-Furanacrylonitrile (7187-01-1)
Cinnamonitrile (4360-47-8)
3-(2-furyl)-2-cyanoacrylic acid
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