Synthesis of 9,10-dihydrophenanthrene

Preparation of 9,10-dihydrophenanthrene

Alternative Names: phenanthrene, 9,10-dihydro-; 9,10-dihydro-phenanthrene

Preparation of 9,10-dihydrophenanthrene (phenanthrene, 9,10-dihydro-; 9,10-dihydro-phenanthrene)

Preparation of 9,10-dihydrophenanthrene (phenanthrene, 9,10-dihydro-; 9,10-dihydro-phenanthrene)

40 g of phenanthrene is hydrogenated with 4 g of copper chromite in 100 ml ethanol at 150° C with a hydrogen pressure of 150-200 atm. The reaction lasts about 3 hours. After the hydrogenation the mixture is fractionated through a Widmer column, the fraction distilling at 176-178°/20 mm is collected. The yield of 9,10-dihydrophenanthrene is  87%. Crude 9,10-dihydrophenanthrene is purified by crystallization from methanol, yielding product, which melts at 33.8-34.4° C. Further hydrogenation of 9,10-dihydrophenanthrene with copper chromite requires a temperature higher by 50-70° C, so it is better to use nickel catalysts for complete hydrogenation of phenanthrene.

J.R. Durland and H. Adkins, J. Amer. Chem. Soc, 59, 135 (1937)

IUPAC Name

9,10-dihydrophenanthrene

InChI

InChI=1S/C14H12/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-8H,9-10H2

InChI Key

XXPBFNVKTVJZKF-UHFFFAOYSA-N

Canonical SMILES

C1CC2=CC=CC=C2C3=CC=CC=C31

Depositor-Supplied Synonyms

9,10-DIHYDROPHENANTHRENE, 776-35-2, Phenanthrene, 9,10-dihydro-, 9,10-dihydro-phenanthrene, XXPBFNVKTVJZKF-UHFFFAOYSA-N, 63818-79-1, NSC60018, ACMC-1BA4Q, UNII-BRM9TU2F34, AC1Q1H8R, BRM9TU2F34, D106003_ALDRICH, AC1L20Y2, AMOT0055, CHEMBL2407181, 37349_FLUKA, MolPort-001-762-094, EINECS 212-278-2, ANW-75582, NSC 60018, NSC-60018, ZINC01689949, AKOS004904703, CD-1135, AJ-30013, AK112574, AN-47585, CJ-28051, KB-74291, SC-48906, DB-007226, TC-164327, AM20041165, D0554, FT-0600670, Phenanthrene, 9,10-dihydro- (8CI)(9CI), ST51056578, A839150, S14-0974, 3B3-015604, InChI=1/C14H12/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)13/h1-8H,9-10H

Removed Synonyms

DIHYDROPHENANTHRENE, Phenanthrene,10-dihydro-, CID13058

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