Synthesis of 1-benzoylnaphthalene (1-naphthyl phenyl ketone)

Preparation of 1-benzoylnaphthalene

Preparation of 1-benzoylnaphthalene (1-naphthyl phenyl ketone)

Preparation of 1-benzoylnaphthalene (1-naphthyl phenyl ketone)

1-benzoylnaphthalene is prepared by carefully heating together in a dry 500 ml flask a mixture of 11.5 ml (or 14 grams) of pure benzoyl chloride (freshly distilled) and 14 grams of anhydrous aluminum chloride. Aluminum chloride partially dissolves in benzoyl chloride and the mixture warms of itself. In order to complete the dissolution, the flask is heated gently over a “soft ” free flame, being careful to avoid overheating. When the particles of aluminum chloride have nearly all disappeared the solution should be deep yellow or brown in color, but it should not show signs of decomposition. The flask to cooled forming a yellow or orange crystalline (intermediate) product. 80 ml of carbon disulfide are added to the solution, warmed gently and cautiously with shaking until the solid is all dissolved. Then the solution is allowed to cool, but without causing the addition compound to crystallize. In portions, 12.8 grams of solid naphthalene are added,  forming the vigorous evolution of hydrogen chloride. The mixture is gently warmed for a few minutes in order to complete the reaction and then cooled thoroughly in an ice bath and rubbed the material against the walls of the flask to cause the dark oil to solidify. The crude dark-colored solid material is collected by filtration, being careful to use a perfectly dry funnel and flask. Then the precipitates are washed with a small quantity of fresh solvent and poured into about 300 ml of water containing 20 ml of concentrated hydrochloric acid. The mixture is heated for about 10 minutes in order to decompose completely the aluminum complex and to expel adhering carbon disulfide, then cooled to room temperature and the oily or semi-solid product is extracted with ether. The ethereal solution is dried with calcium chloride, decolorized by treating with a small quantity of activated carbon, filtered, and the ether removed by evaporation. The residual oil solidifies on cooling, and the product is best purified by crystallizing from ethanol or methanol and allowing crystallization to proceed slowly yielding 18 of final compound, which melts at 76° C. The isomeric 2-naphthyl phenyl ketone melts at 82° C.

Experiments in Organic Chemistry, L. F. Fieser, 194-196, 1941

IUPAC Name

naphthalen-1-yl(phenyl)methanone

InChI

InChI=1S/C17H12O/c18-17(14-8-2-1-3-9-14)16-12-6-10-13-7-4-5-11-15(13)16/h1-12H

InChI Key

CXAYOCVHDCXPAI-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(=O)C2=CC=CC3=CC=CC=C32

MeSH Synonyms

2-naphthylphenylketone, naphthyl phenyl ketone

Depositor-Supplied Synonyms

1-Benzoylnaphthalene, 1-NAPHTHYL PHENYL KETONE, 642-29-5, Benzoylnaphthalene, alpha-BENZOYLNAPHTHALENE, Naphthyl phenyl ketone, (naphthalen-1-yl)(phenyl)methanone, 1-naphthyl(phenyl)methanone, MLS002637931, Methanone, 1-naphthalenylphenyl-, ST50411287, naphthylphenylketone, ACMC-20aot2, AC1Q5CVV, AC1Q5CWG, AC1Q5GBL, AC1L2C0T, 1-NAPHTHYLPHENYLKETONE, SCHEMBL547632, Napthalen-1-yl-phenyl-methanone, CHEMBL1709527, naphthalen-1-yl(phenyl)methanone, NSC6729, CXAYOCVHDCXPAI-UHFFFAOYSA-N, MolPort-001-815-054, HMS3093G06, NSC-6729, EINECS 211-382-5, AR-1C1650, ZINC01845878, AKOS005920031, MCULE-5026457870, NE42786, VZ21174, BP-12673, CJ-30166, SMR001547442, AI3-04214, DB-054630, KB-152165, TC-171821, FT-0632728, EN300-73199, AE-641/00364022, 3B3-015740

Removed Synonyms

CID69503, 6623-18-3

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