Org. Synth. 1938, 18, 59
DOI: 10.15227/orgsyn.018.0059
1,2-NAPHTHALIC ANHYDRIDE
[1,2-Naphthalenedicarboxylic anhydride]
Submitted by E. B. Hershberg and Louis F. Fieser.
Checked by C. R. Noller and S. Kinsman.
1. Procedure
In a
50-cc. Claisen distilling flask with a
50-cc. sealed-on distilling flask as a receiver are placed
20 g. (0.1 mole) of 3,4-dihydro-1,2-naphthalic anhydride (p. 194) and
3.2 g. (0.1 gram atom) of sulfur. After the flask is immersed in a bath
(Note 1) previously heated to 230–235° and shaken until the globule of
sulfur has dissolved (fifteen to twenty minutes), the temperature is raised to 250° for thirty minutes
(Note 2). The residue is distilled under reduced pressure
(Note 3), and the distillate is crystallized from
150 cc. of benzene to which
50 cc. of ligroin (b.p.
60–80°) has been added at the boiling point. The yield is
15–18 g. (
76–91 per cent of the theoretical amount) of light yellow needles melting at
166–167°.
2. Notes
1.
A
Wood's metal bath or a mixture (m.p. about 150°) of ten parts of
potassium nitrate and seven and one-half parts of
sodium nitrite may be used.
2.
If the heating at 250° is continued until
hydrogen sulfide is no longer evolved (about ten hours), the product, after recrystallization, is lighter in color and shrinks less before melting.
3.
The material comes over between 210° and 215° at 12–13 mm. with the bath at 260°.
3. Discussion
1,2-Naphthalic anhydride has been prepared by the hydrolysis of the
dinitrile of 1,2-naphthalic acid;
1 by the oxidation of suitably substituted hydrocarbons or ketones;
2 and by the dehydrogenation of the 3,4-dihydro compound with
bromine3 or with
sulfur.
4
This preparation is referenced from:
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
ligroin
dinitrile of 1,2-naphthalic acid
Benzene (71-43-2)
hydrogen sulfide (7783-06-4)
bromine (7726-95-6)
sodium nitrite (7632-00-0)
sulfur (7704-34-9)
potassium nitrate (7757-79-1)
3,4-Dihydro-1,2-naphthalic anhydride (37845-14-0)
1,2-Naphthalic anhydride,
1,2-Naphthalenedicarboxylic anhydride (5343-99-7)
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