Org. Synth. 1938, 18, 59
Submitted by E. B. Hershberg and Louis F. Fieser.
Checked by C. R. Noller and S. Kinsman.
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
) has been added at the boiling point. The yield is 15–18 g.
per cent of the theoretical amount) of light yellow needles melting at 166–167°
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.
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.
The material comes over between 210° and 215° at 12–13 mm. with the bath at 260°.
has been prepared by the hydrolysis of the dinitrile of 1,2-naphthalic acid
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
This preparation is referenced from:
Chemical Abstracts Nomenclature (Collective Index Number);
dinitrile of 1,2-naphthalic acid
hydrogen sulfide (7783-06-4)
sodium nitrite (7632-00-0)
potassium nitrate (7757-79-1)
3,4-Dihydro-1,2-naphthalic anhydride (37845-14-0)
1,2-Naphthalenedicarboxylic anhydride (5343-99-7)
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