Organic Syntheses, CV 2, 382
Submitted by R. L. Shriner, S. G. Ford, and L. J. Roll.
Checked by C. R. Noller
1. Procedure
A mixture of
100 g. (0.89 mole) of citraconic anhydride (Note
1) 100 cc. of water, and
150 cc. of dilute nitric acid (1 part of concentrated nitric acid to 4 parts of water by volume) is evaporated in a
500-cc. Erlenmeyer flask until the appearance of red fumes (Note
2). The solution is cooled and the
mesaconic acid is collected on a filter. The mother liquor is evaporated to 150 cc., cooled, and the crystalline solid which separates is collected on a filter. Further concentration of the mother liquor to 50 cc. yields more product (Note
3). The entire product is recrystallized from 100 cc. of water. The yield of
mesaconic acid melting at
203–205° is
50–60 g. (
43–52 per cent of the theoretical amount).
2. Notes
1. An equivalent amount of
citraconic acid can be used. Directions for preparing
citraconic acid and anhydride are given on
p. 140.
2. It is necessary to carry the evaporation to the point where red fumes appear in order for the rearrangement to take place. The volume is usually about 250 cc.
3. The concentration of the mother liquor must be carried out in steps in order to obtain an efficient separation of
mesaconic acid.
3. Discussion
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