Synthesis of anthracene

Preparation of anthracene

Preparation of anthracene

Preparation of anthracene

Pieces of porous pumice stone of a size that will conveniently pass into a combustion tube are added to a paste prepared from 100 g of good zinc dust and 30 ml of alcohol. The mixture is stirred to incorporate the pumice and paste. They are removed from the paste with tongs, and heated in a porcelain dish with constant motion over a free flame until the alcohol is evaporated. A hard glass combustion tube, 70 cm long, is drawn out at one end to a narrow tube, the narrowed end is closed by a loose plug of asbestos, and a layer of zinc dust, 5 cm long, is placed next to the plug, then a mixture of 2 g of quinizarin, alizarin, or anthraquinone with 20 g (excess) of zinc dust, and finally a layer of pumice zinc dust, 30 cm long. After a canal has been formed over the zinc dust by placing the tube in a horizontal position and tapping it, the latter is transferred to a combustion furnace, and a rapid current of dry hydrogen is passed through the tube without heating. The open end of the tube is closed by a one-holed cork, and the issuing gas led to a draught pipe. After the gas has been passed for some time a test tube of the issuing gas is collected over water at intervals, and a light applied to the mouth of the test tube at least 3-4 meters from the apparatus. When the contents of the tube burn quietly, all the air has been displaced from the apparatus. The gas current is then diminished to about 150 ml per minute, and the pumice zinc dust is heated with small flames. (On no account must the apparatus be heated until all the air has been displaced.) The heating is gradually increased from the front backwards, until finally the tube is heated as strongly as possible. The rear layer of 5 cm of zinc dust is next similarly heated, and when this glows, the mixture of anthracene derivative and zinc dust is gradually heated, all being done as in the estimation of nitrogen. The anthracene formed condenses to crystals in the forward cool part of the tube. After the reaction is complete, a rapid current of hydrogen is passed while the tube is cooling; the part containing the anthracene, when cold, is broken off and the substance removed with a small spatula; it is purified by sublimation. Yield almost theoretical (1.5 g). Colourless crystals; insoluble in water; soluble in warm benzene and in glacial acetic acid; m.p. 213°  C; b.p. 351° C; It is better to use alcohol in making zinc dust paste, for if there is much oxide present in the dust a great deal of heat may be evolved on adding water, and much oxidation of the metal occur.

Systematic organic chemistry, by W. M. Cumming, 152-154, 1937.

IUPAC Name

anthracene

InChI

InChI=1S/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10H

InChI Key

MWPLVEDNUUSJAV-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C=C3C=CC=CC3=CC2=C1

MeSH Synonyms

anthracene, anthracene, sodium salt, ion (1-)

Depositor-Supplied Synonyms

ANTHRACENE, 120-12-7, Paranaphthalene, Anthracin, Green Oil, Tetra Olive N2G, Anthracen, Anthracen [German], Anthrazen, Bis-alkylamino anthracene, CHEBI:35298, Anthracene, pure, CCRIS 767, HSDB 702, Anthracene oil (coal tar fraction), NSC 7958, EINECS 204-371-1, UNII-EH46A1TLD7, A89200_ALDRICH, 40076_SUPELCO, 48567_SUPELCO, 48647_SUPELCO, AI3-00155, 46051_RIEDEL, WLN: L C666J, 10580_FLUKA, NSC7958, MWPLVEDNUUSJAV-UHFFFAOYSA-N, Anthracene solution, 141062_SIAL, Coal tar pitch volatiles: anthracene, NCGC00163972-01, ST093055, DSSTox_CID_3878, C14315, DSSTox_RID_77216, DSSTox_GSID_23878, AN3, CAS-120-12-7, acene, acenes, polyacenes, Acen, Anthracene oil, Azen, p-Naphthalene, anthracen-1-yl, anthracen-2-yl, anthracen-9-yl, Deuterated anthracene, HRACENE, Sterilite hop defoliant, PubChem22168, AC1L1QYH, ANTHRACENE- D10, Epitope ID:119716, EH46A1TLD7, KSC174Q2B, ANTHRACENE, SCINTILLATOR, 141062_ALDRICH, 331481_ALDRICH, ACMC-1C338, CHEMBL333179, CHEBI:35297, CTK0H4820, MolPort-001-760-592, Anthracene, labeled with deuterium, Coal tar pitch volatiles:anthracene, NSC-7958, ZINC1586329, Tox21_202226, Tox21_300014, ANW-17457, BBL005251, BDBM50060894, LS-627, SBB058663, STK398386, ZINC01586329, AKOS000119970, AC-5799, DB07372, MCULE-4141881437, RP23973, RTR-003345, NCGC00163972-02, NCGC00163972-03, NCGC00254204-01, NCGC00259775-01, AJ-27544, AK157086, AN-10591, KB-74701, L975, PL000103, PL015194, PL016287, PL052853, AB1002596, TL8000534, TR-003345, A0405, A0495, A0992, FT-0622409, H2412, ST24045970, A804437, I14-0862, J-200085, UNII-0TNN3Q0D4D component MWPLVEDNUUSJAV-UHFFFAOYSA-N, InChI=1/C14H10/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-10, 54261-80-2

Removed Synonyms

null, (2H10)Anthracene, 9,10-DIHYDROANTHRACENE, CID8418, anthracene, sodium salt, ion (1-), c0991, C034020, 613-31-0, 1719-06-8

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