urbaf2

NITRO DERIVATIVES OF NAPHTHALENE^441

thalene, a dinitro-product and an oil as the products of nitration. Medinaveitia

and de Buruaga [39] also used a mixture of nitric and sulphuric acids and obtained

polynitro compounds.

A number of other authors have carried out the nitration of 2-methylnaphtha-

lene, mainly as a step in the preparation of a new intermediate for dyes. Lesser,

Glasser and Aczel [40] nitrated 2-methylnaphthalene in the presence of acetic acid

and Vessely and Kapp [41] used nitric acid alone at low temperature (5-15°C).

They obtained a 58% yield of 1-nitro-2-methylnaphthalene and an oil which contained

4-Nitro-, 6-nitro- and 8-nitro-2-methylnaphthalenes. Vessely and his co-workers

[42, 43] identified qualitatively most of the mononitro derivatives of 2-methyl-

naphthalene and their reduction products.

The most extensive work on the subject so far has been carried out by Brink

and Shrieve [44]. The highest yield of 2-methyl-1-nitronaphthalene they obtained

was 57% of the theoretical. This was produced by nitrating 2-methylnaphthalene

at low temperatures (0-30°C) with a 70% excess of 70% nitric acid. The other

isomers appeared as a by-product oil. When using a 15% excess of a nitrating

mixture composed of 25% HNO 3 , 55% H 2 SO 4 and 20% H 2 O the yield of l-nitro-

2-methylnaphthalene was also 57%. Dinitration took place when acetic anhydride

was used. The product was in the form of a solid with m. p. 209-213°C. No deter-

mination of the structure of the dinitroproducts was carried out.

LITERATURE

1. H. E. ARMSTRONG and W. P. WYNNE, Ber. 25, 226 (1892); 32, 1136 3189 (1899); Ann. 361,
   170 (1908).


2. N. DONALDSON, The Chemistry and Technology of Naphthalene Compounds, Arnold, London,
   1958.


3. H. H.-HODGKIN and E. R. WARD, J. Soc. Dyers and Colourists 63, 141 (1947).


4. W. LENZE, Jahresber. Mil. Vers-Amts. 2, 7 (1895).


5. A. FRANK, Beitr. Augenheilkunde 31, 93 (1898).


6. HANKE, Wiener Klin. Wochenschr. 12, 275 (1899).


7. SILEX, Z. Augenheilkunde. 5, 178 (1902).


8. L. CASPAR, Klin. Mbl. Augenheilkunde 59, 112 (1913).


9. A. LAURENT, Ann. Chim. [2], 59, 376 (1835); [3], 3, 195 (1842); Ann. 41, 98 (1842); 43,
   200 (1842).


10. R. PIRIA, Ann. 78, 31 (1851).


11. Z. ROUSSIN, Compt. rend. 52, 796 (1861).


12. L. TROOST, Bull. soc. chim. France 3, 75 (1861); Jahresber. 1861, 644.


13. L. DARMSTÄDTER and H. WICHELHAUS, Ann. 152, 301 (1899).


14. A. A. D’AGUIAR, Ber. 2, 220 (1869); 5, 370 (1872).


15. F. K. BEILSTEIN and A. KIJHLBERG, Ann. 169, 81 (1873).


16. F. K. BEILSTEIN and A. KURBATOV, Ann. 202, 217 (1880).


17. W. WILL, Ber. 28, 367 (1895).


18. P. FRIEDLÄNDER, Ber. 32: 3531 (1899).
    18a. O. DIMROTH and F. RUCK, Ann. 446, 123 (1925).