Synthesis of 3-acetylphenanthrene

Preparation of 3-acetylphenanthrene

Preparation of 3-acetylphenanthrene

Preparation of 3-acetylphenanthrene

132 g of anhydrous aluminum chloride are added slowly to 600 g of nitrobenzene, and the resulting solution is added to a solution of 80 g of phenanthrene in 240 g of nitrobenzene. The resulting solution is cooled in an ice bath, and 48 g of freshly distilled acetyl chloride is added in one portion. After 30 minutes in the ice bath and 6-7 hours standing at room temperature, the reaction mixture is poured into excess crushed ice containing 80 ml of hydrochloric acid. The combined product from five such runs is steam-distilled for removal of the nitrobenzene. The residue after removal of the nitrobenzene is distilled, and the fraction boiling in the range 180-214°/4 mm. pressure is collected. The distillate is digested with ether, the ethereal solution dried, and the solvent distilled off. The residue is recrystallized from methanol to give 315 g (65 %) of 3-acetylphenanthrene, m.p. 72°C. The solid material remaining undissolved during the ether digestion above is distilled twice at 2-3 mm. pressure, and the solid distillate is recrystallized from benzene. There is obtained 75 g. (15%) of the isomeric 2-acetylphenanthrene, m.p. 143°.

J. Am. Chem. Soc., 52, 3707 (1930)

ibid., 58, 2099 (1936)

IUPAC Name

1-phenanthren-3-ylethanone

InChI

InChI=1S/C16H12O/c1-11(17)14-9-8-13-7-6-12-4-2-3-5-15(12)16(13)10-14/h2-10H,1H3

InChI Key

JKVNPRNAHRHQDD-UHFFFAOYSA-N

Canonical SMILES

CC(=O)C1=CC2=C(C=CC3=CC=CC=C32)C=C1

Depositor-Supplied Synonyms

3-Acetylphenanthrene, 2039-76-1, 1-(phenanthren-3-yl)ethanone, 1-(3-Phenanthryl)ethanone, Ethanone, 1-(3-phenanthrenyl)-, 1-phenanthren-3-ylethanone, Ketone, methyl 3-phenanthryl, JKVNPRNAHRHQDD-UHFFFAOYSA-N, 1-(phenanthren-3-yl)ethan-1-one, Methyl 3-phenanthryl ketone, AC1L2MTA, AC1Q5GQY, ACMC-1CLH9, DSSTox_CID_29099, DSSTox_RID_83318, DSSTox_GSID_49243, SCHEMBL50671, A19407_ALDRICH, KSC492K8T, 1-(3-Phenanthryl)ethanone #, 1-(3-phenanthryl)ethan-1-one, CHEMBL3186759, CTK3J2589, JKVNPRNAHRHQDD-UHFFFAOYSA-, NSC3192, MolPort-001-791-992, KST-1B1600, NSC-3192, ZINC1037154, EINECS 218-020-5, Tox21_202956, 0457AB, ANW-63232, AR-1B1586, SBB062758, STK366110, ZINC01037154, AKOS004908916, CA-1145, MCULE-1366015107, RTX-010233, TRA0028945, VZ26229, NCGC00260502-01, AJ-24728, AK-87890, CJ-04680, KB-70323, OR088647, PL001280, ZB015680, CAS-2039-76-1, AB0052749, DB-022171, FT-0082775, FT-0614888, ST24037642, I14-14285, 3B3-015605, InChI=1/C16H12O/c1-11(17)14-9-8-13-7-6-12-4-2-3-5-15(12)16(13)10-14/h2-10H,1H3

Removed Synonyms

CID74867, 20810-22-4

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