Org. Synth. 1932, 12, 46
DOI: 10.15227/orgsyn.012.0046
MERCURY DI-β-NAPHTHYL
[Mercury, di-2-naphthyl-]
Submitted by A. N. Nesmajanow and E. D. Kohn.
Checked by Frank C. Whitmore and R. W. Beattie.
1. Procedure
In a
2-l. round-bottomed flask, equipped with a stirrer, are placed
231 g. (0.5 mole) of the addition compound of β-naphthalenediazonium chloride and mercuric chloride (p. 432),
700 cc. of acetone (b.p.
55–57°) and
189 g. (3 moles) of copper powder (Note 1). The mixture is quickly cooled to 20° and stirred for one hour.
Seven hundred cubic centimeters of concentrated aqueous ammonia solution (sp. gr. 0.9) is added, mixed well, and allowed to stand overnight. The supernatant liquid is decanted; the solid is collected on a
Büchner funnel and washed successively with
25-cc. portions of water, acetone, and ether. After air-drying, the crude material is recrystallized from
xylene, using
decolorizing carbon. The crystals thus obtained are slightly yellow
(Note 2) and melt at
241.5–243.5°. The yield is
51–55 g. (
45–48 per cent of the theoretical amount based on the addition compound used)
(Note 3).
2. Notes
1.
The same notes apply as in the preparation of
β-naphthylmercuric chloride (p. 432).
2.
The product from this reaction is never pure white. Colorless
mercury di-β-naphthyl can be prepared in good yield from
β-naphthylmercuric chloride (p. 432) and
sodium iodide, according to the directions given in
Org. Syn. Coll. Vol. I, 1941, 231, for
mercury di-p-tolyl.
13.
Similar results are obtained with other aromatic amines;
aniline and
p-iodoaniline yield
mercury diphenyl and
mercury di-p-iodophenyl.
3. Discussion
Mercury di-β-naphthyl has been prepared by the action of
sodium amalgam on
β-bromonaphthalene,
2 and by the action of alcoholic
sodium iodide on
β-naphthylmercuric chloride.
1
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
Mercury di-β-naphthyl
β-Naphthylmercuric chloride
mercury diphenyl
mercury di-p-tolyl
mercury di-p-iodophenyl
ammonia (7664-41-7)
ether (60-29-7)
aniline (62-53-3)
copper powder (7440-50-8)
acetone (67-64-1)
decolorizing carbon (7782-42-5)
sodium (13966-32-0)
β-bromonaphthalene (580-13-2)
mercuric chloride (7487-94-7)
xylene (106-42-3)
sodium iodide (7681-82-5)
Mercury, di-2-naphthyl- (19510-26-0)
β-naphthalenediazonium chloride
p-IODOANILINE (540-37-4)
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