Organic Syntheses, CV 2, 560
[I]
Submitted by Louis F. Fieser and E. L. Martin.
Checked by C. R. Noller
1. Procedure
In a
1-l. round-bottomed flask, fitted with a
reflux condenser attached to a
gas trap, are placed
118 g. (1 mole) of succinic acid and
215 cc. (235 g., 3 moles) of acetyl chloride. The mixture is gently refluxed on the
steam bath until all the acid dissolves; this requires one and a half to two hours. The solution is allowed to cool undisturbed and is finally chilled in an
ice bath. The
succinic anhydride, which separates in beautiful crystals, is collected on a
Büchner funnel, washed with two
75-cc. portions of ether, and dried in a
vacuum desiccator. The yield of material melting at
118–119° is
93–95 g. (
93–95 per cent of the theoretical amount).
[II]
Submitted by R. L. Shriner and H. C. Struck.
Checked by C. R. Noller, F. B. Hilmer, and J. D. Pickens.
1. Procedure
Two hundred thirty-six grams (2 moles) of succinic acid (Note
1) and
153.5 g. (1 mole) of phosphorus oxychloride are placed in a
1-l. Claisen flask. One neck of the flask is equipped with a reflux condenser connected to a gas trap; the other neck and the side arm of the flask are closed with
corks. The mixture is heated (Note
2) with a free flame for about fifty minutes until no more
hydrogen chloride is evolved. The condenser is removed and the flask is arranged for distillation, with a tube leading from the side arm of the
receiver to the drain in order to carry off the vapors. A few cubic centimeters of distillate is collected below 255°, at which temperature the receiver is changed and
succinic anhydride is collected from
255–260° (Note
3). The product melts at
118–120° and weighs
164–192 g. (
82–96 per cent of the theoretical amount).
The
succinic anhydride may be purified by dissolving
50 g. of the crude material in
35 cc. of acetic anhydride. The hot solution is cooled in an ice bath. The crystals are filtered with suction, washed with two
20-cc. portions of cold, absolute ether, and air-dried quickly at 40°. The yield of the pure anhydride, which melts at
119–120°, is
43.5 g.
2. Notes
1.
Succinic acid having a melting point of
189–190° was used. Less pure material gives a lower-melting product.
2. The reaction foams considerably at the start, hence slow and careful heating is necessary. It is best to heat the flask directly with the flame, making certain that all parts of the mixture are heated about equally.
3. The tarry mass left in the distilling flask may be easily removed by warm dilute
sodium hydroxide.
3. Discussion
Succinic anhydride has been prepared from
succinic acid with
phosphorus pentachloride,
1,
2 phosphorus oxychloride,
2,
3 phosphorus pentoxide,
4 thionyl chloride,
5 acetyl chloride,
3,
6,
7 or
succinyl chloride;
8 from
barium or sodium succinate with
benzoyl chloride,
1 acetyl chloride,
9 acetic anhydride,
10 or
benzophenone dichloride;
11 from
succinyl chloride and
oxalic acid6 or
sodium acetate;
9 and from
ethyl succinate and
benzoyl chloride.
12
This preparation is referenced from:
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