A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Org. Synth. 1932, 12, 46
DOI: 10.15227/orgsyn.012.0046
[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.1
3. 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

References and Notes
  1. Private communication, Frank C. Whitmore and R. J. Sobatzki.
  2. Chattaway, J. Chem. Soc. 65, 878 (1894); Michaelis, Ber. 27, 251 (1894).

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)