Garlock, Edward A. Jr. published the artcileAnthracene series. I. Methyl ketones and carbinolamines derived from 1,2,3,4-tetrahydroanthracene, HPLC of Formula: 52358-73-3, the publication is Journal of the American Chemical Society (1945), 2255-9, database is CAplus and MEDLINE.
Anthracene (I) (89 g.), 5 g. Cu chromite, and 300 cc. decalin, shaken with H at 2300 lb. and 250° for 24 min., give 43% of the 1,2,3,4-tetrahydro derivative (II); reduction at 1500 lb. and 130° gives 25% of II. Reduction of I at 2300 lb. and 150° for 5 min. gives 95% of the 9,10-dihydro derivative AcCl (20.5 cc.) and 60 g. AlCl3 in 190 cc. PhNO2 at -3° to -7°, treated slowly with 45.5 g. of II in 145 cc. PhNO2, with stirring at 5° for 20 h., the resulting oil distilled at 0.1 mm. (160-70°), and crystallized from 200 cc. ligroin, give 17.6 g. of 6-acetyl-1,2,3,4-tetrahydroanthracene (III), m. 101-2°, and, from the mother liquor, 13.5 g. of the 5-isomer (IV), nD25 1.6333 (isolated as the semicarbazone, m. 209-11°). III yields a semicarbazone, m. 251.5-2.5°; an oxime, m. 165.5-7°; and a picrate, light yellow, m. 118-20°. III (4.4 g.) in 25 cc. AcOH, treated with 5 g. CrO3 in 3 cc. H2O and 22 cc. AcOH at 50°, warmed to 60° for 10 min. and allowed to stand at room temperature for 1 h., gives 2.2 g. of 6-acetyl-1,2,3,4-tetrahydro-9,10-anthraquinone, yellow, m. 169-70°. III (8.96 g.) in 260 cc. EtOH at 5°, treated dropwise with 2.1 cc. Br, gives 8 g. of the 6-(ω-bromoacetyl)derivative (V), light yellow, m. 113.5-15°. III (1.1 g.), reduced with 6.5 cc. of 3 N (iso-PrO)3Al in iso-PrOH for 15 min., gives 0.9 g. of the 6-(1-hydroxyethyl) derivative, m. 87.5-8.5°. III (2.2 g.), 10 g. amalgamated Zn, 20 cc. AcOH, 20 cc. concentrated HCl, and 8 cc. PhMe, refluxed 24 h. (three 6-cc. portions of concentrated HCl added during this period), give 1.9 g. of 6-ethyl-1,2,3,4-tetrahydroanthracene, m. 38-9.5° (picrate, bright red, m. 100-1°, very unstable). III (3.3 g.), refluxed with alk. NaOCl for 2 h., gives 2.8 g. of 1,2,3,4-tetrahydro-6-anthracenecarboxylic acid, m. 264-6°; Et ester (VI), m. 113°. Dehydrogenation of III gives 2-acetylanthracene and of VI gives Et 2-anthroate. V (6.06 g.) in 50 cc. absolute ether, treated with 6.38 g. Am2NH, shaken for 3 h., and reduced with 30 cc. 3 N (iso-PrO)3Al in iso-PrOH, gives 3.5 g. of 6-(2-diamylamino-1-hydroxyethyl)-1,2,3,4-tetrahydroanthracene-HCl, m. 114.5-16°; the diheptylamino homolog m. 114.5-16.5°; the dinonylamino homolog m. 112-16°. IV forms an oxime, m. 120.5-2.5°, and a picrate, light yellow, m. 115-16°. Oxidation of IV with CrO3 in AcOH gives 5-acetyl-1,2,3,4-tetrahydro-9,10-anthraquinone, light yellow, m. 122-4°. Reduction of IV with (iso-PrO)3Al in iso-PrOH gives 5-(1-hydroxyethyl)-1,2,3,4-tetrahydroanthracene, m. 73.5-6.5°. Oxidation of IV with NaOCl gives 1,2,3,4-tetrahydro-5-anthracenecarboxylic acid, m. 190-6°; Et ester, m. 64-70°. Dehydrogenation of IV gives 1-acetylanthracene. In the reaction of I and AcCl in C2H2Cl4, the formation of III is almost entirely suppressed and the oily ketone (IV) is formed in approx. the same yield as in the PhNO2 experiment
Journal of the American Chemical Society published new progress about 52358-73-3. 52358-73-3 belongs to bromides-buliding-blocks, auxiliary class Bromide,Naphthalene, name is 1,3-Dibromonaphthalene, and the molecular formula is C10H6Br2, HPLC of Formula: 52358-73-3.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary