A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Org. Synth. 1931, 11, 40
DOI: 10.15227/orgsyn.011.0040
[Pyruvic acid, cyanophenyl-, ethyl ester]
Submitted by Roger Adams and H. O. Calvery.
Checked by J. B. Conant and Doris Blumenthal.
1. Procedure
In a 3-l. round-bottomed flask, fitted with a reflux condenser, is placed 650 cc. of absolute alcohol (Note 1), and to it 46 g. (2 gram atoms) of sodium is added as rapidly as possible without loss of material through the condenser. If the sodium does not entirely dissolve, heat is applied. To the hot sodium ethoxide solution 312 g. (2.1 moles) of ethyl oxalate (Org. Syn. Coll. Vol. I, 1941, 261) is added as rapidly as possible. Then, immediately, 234 g. (2 moles) of benzyl cyanide (Org. Syn. Coll. Vol. I, 1941, 107) is added, and the reaction mixture is allowed to stand overnight. The solution is transferred to a 3-l. beaker and treated with 250–300 cc. of water (Note 2). It is then warmed to 35° and made strongly acid to litmus with concentrated hydrochloric acid. Mechanical stirring is used during the acidification. On cooling to ordinary temperatures the ester crystallizes. The yield is 360–385 g. of lemon-yellow crystals melting at 126–128°. On recrystallization from 60 per cent alcohol, the ester melts at 130°. The final yield is 300–325 g. (69–75 per cent of the theoretical amount).
2. Notes
1. Absolute alcohol, prepared according to the directions in Org. Syn. Coll. Vol. I, 1941, 259, is satisfactory.
2. This amount of water dilutes the alcohol so that the ester crystallizes well. If more water is used an oily product separates and then solidifies.
3. Discussion
The only method of preparation mentioned in the literature is that given above.1
This preparation is referenced from:

References and Notes
  1. Erlenmeyer, Ann. 271, 173 (1892).

Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)

alcohol (64-17-5)

hydrochloric acid (7647-01-0)

sodium (13966-32-0)

sodium ethoxide (141-52-6)

Benzyl cyanide (140-29-4)

Ethyl oxalate

Ethyl phenylcyanopyruvate,
Pyruvic acid, cyanophenyl-, ethyl ester (6362-63-6)