Synthesis of diphenylmethane

Preparation of diphenylmethane

Preparation of diphenylmethane from benzophenone

Preparation of diphenylmethane from benzophenone

Preparation of diphenylmethane from benzophenone

To the round bottom flask connected with the gas inlet 20 g of benzophenone are dissolved and boiled under a reflux condenser in 200 g of ethanol.  Then 20 g of metallic sodium slowly added to the boiling solution in small peaces. When all the sodium has dissolved, the contents of the flask are saturated with carbon dioxide and then poured into cold water and the whole extracted with benzene. The benzene solution is dried over calcium chloride and distilled off. Further distillation is carried on under reduced pressure. The diphenyl methane passes over at 174-176° C at 80 mm Hg and solidifies in the receiver as a colorless needles with melting point 25-26°  yielding 90 % of diphenylmethane.

Preparation of organic compounds, E. de. Barry Barnett, 41-42, 1912

Preparation of diphenylmethane from benzene and benzyl chloride

Preparation of diphenylmethane from benzene and benzyl chloride

Preparation of diphenylmethane from benzene and benzyl chloride

For the preparation of diphenylmethane 1 g of aluminium foil in thin strips is treated for one to two minutes with a concentrated solution of mercuric chloride and then rinsed thoroughly, first with cold distilled water, then with absolute ethanol, and finally with dry benzene. The cleaned aluminium is transferred as rapidly as possible, to the flask containing 65 g of dry benzene. From the dropping funnel during 1 hour period 30 g of benzyl chloride are slowly added dropwise to the benzene. The reaction starts with rise of temperature and evolution of hydrochloric acid. When all the benzyl chloride has been added, the reaction mixture is heated for 15 min, then cooled, shaken up with solution of sodium hydroxide, and the benzene layer separated. The aqueous portion additionally is extracted with benzene, the benzene solutions combined, dried over calcium chloride, and the organic solvent removed by distillation. The residue is then fractionated under reduced pressure, the diphenyl methane passing over at 174-176° C at 80 mm of Hg forming colorless needles with melting point 25-26° C and boiling point 262° C. The final yield is about 20 %.

Preparation of organic compounds, E. de. Barry Barnett, 44, 1912

Preparation of diphenylmethane from benzene and benzyl alcohol

Preparation of diphenylmethane from benzene and benzyl alcohol

Preparation of diphenylmethane from benzene and benzyl alcohol

A mixture of equal weights of concentrated sulfuric acid and glacial acetic acid is run into a mixture of 10 g of benzyl alcohol, 27 g (excess) of benzene and 100 g of glacial acetic acid until most of the benzene has separated on the surface. After 12 hours, 500 g of concentrated sulfuric acid are added under constant cooling, and the mixture again allowed to stand for 6 hours. The mass is then poured into water, extracted with ether, the extract dried over calcium chloride, and the residue, after removing the ether on a water bath, fractionated under reduced pressure, the fraction 174-176°C/30mmHg being separately collected. Yield 25% theoretical (4 g). Colourless oil; on cooling solidifies to needle-shaped crystals ; orange-like odour ; m.p. 26° C; b.p. 263° C (175° C/30mm);  d=1.0056 g/ml at 20° C.

Systematic organic chemistry, by W. M. Cumming, 56-57, 1937.

Preparation of diphenylmethane

Preparation of diphenylmethane

10 g of benzophenone, 12 g of hydriodic acid (b.p. 127° C) and 2 g of red phosphorus are heated together in a sealed tube for 6 hours at 160° C. The reaction mixture is extracted with ether and the extract washed with water several times. It is then filtered, dried over calcium chloride for 24 hours, the ether removed on a water bath and the residue distilled. Yield theoretical.

 Systematic organic chemistry, by W. M. Cumming, 177, 1937.

IUPAC Name

benzylbenzene

InChI

InChI=1S/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H2

InChI Key

CZZYITDELCSZES-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CC2=CC=CC=C2

MeSH Synonyms

diphenylmethane

Depositor-Supplied Synonyms

Diphenylmethane, Benzylbenzene, 101-81-5, Ditan, Ditane, Benzene, 1,1′-methylenebis-, Diphenyl methane, Benzene, benzyl-, Methane, diphenyl-, 1,1′-Dimethylenebis(benzene), Benzene, (phenylmethyl)-, Benzyl benzene, 1,1′-methylenedibenzene, Methylenedibenzene, phenylmethylbenzene, (phenylmethyl)benzene, 1,1′-METHYLENEBISBENZENE, Toluene, alpha-phenyl-, NSC 4708, Toluene, .alpha.-phenyl-, CHEMBL1796022, CHEBI:38884, HSDB 5141, CZZYITDELCSZES-UHFFFAOYSA-N, EINECS 202-978-6, AI3-28021-X, AI3-00748, Benzylphenyl, Diphenylmethan, benzyl-benzene, alpha-phenyltoluene, Benzene,1′-methylenebis-, AC1O5E2T, WLN: R1R, ACMC-1C6S2, DSSTox_CID_21891, DSSTox_RID_79869, Methane, diphenyl- (8CI), UNII-K3E387I0BC, DSSTox_GSID_41891, KSC235Q6B, BIDD:ER0257, D209317_ALDRICH, AC1L1P34, K3E387I0BC, 43100_FLUKA, CTK1D5860, NSC4708, MolPort-001-738-538, LTBB002310, NSC-4708, Tox21_301147, ANW-14531, AKOS000120567, RP23108, RTR-000441, NCGC00248307-01, NCGC00255045-01, AJ-29600, AK105938, AN-24585, CAS-101-81-5, CJ-27561, KB-50146, LS-30786, M338, SC-15759, TR-000441, D0896, FT-0625274, ST24046645, A800459, I14-4537, 3B3-033849, InChI=1/C13H12/c1-3-7-12(8-4-1)11-13-9-5-2-6-10-13/h1-10H,11H

Removed Synonyms

Diphenylmethyl, Diphenylmethyl radical, CID7580, 4471-17-4

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1 comment

  1. Arockiaraj.M

    this is really a helpful website .here we can get almost all the preperation methods for organic compounds and the preparation methods of organic compounds which are not available in other website also available here…..so plz make use of it…..

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