Synthesis of o-(3-acenaphthoyl)-benzoic acid

Preparation of 2-(1,2-dihydroacenaphthylen-5-ylcarbonyl)benzoic acid (o-(3-acenaphthoyl)-benzoic acid)

Preparation of 2-(1,2-dihydroacenaphthylen-5-ylcarbonyl)benzoic acid (o-(3-acenaphthoyl)-benzoic acid)

Preparation of 2-(1,2-dihydroacenaphthylen-5-ylcarbonyl)benzoic acid (o-(3-acenaphthoyl)-benzoic acid)

15 grams of acenaphthene and 15 grams of phthalic anhydride are dissolved in 75 ml of purified tetrachloroethane by heating in a 500 ml long-necked, round bottomed flask designed for efficient steam distillation. No condenser is required during the reaction but the flask should be provided with a tube to conduct hydrogen chloride to a gas trap. The solution is cooled until the temperature registers 5° (some solid may separate) and, keeping the flask in the ice bath, 30 grams of aluminum chloride are added. The obtained solution is mixed thoroughly with good cooling for 10 minutes, the flask is removed from the cooling bath by allowing the reaction to proceed at room temperature for one-half hour with frequent shaking, when the addition compound should have separated as a stiff paste. While shaking the flask in the ice bath, small pieces of ice are added, one at a time waiting after each addition until the last piece has reacted. Too rapid addition of ice may cause very vigorous boiling. When the ice no longer produces much reaction and about 100 ml has been added, 20 ml of concentrated hydrochloric acid are added, together with enough water to make the flask half full. The excess tetrachloroethane is then removed by steam distillation, and it is separated from the water layer. The o-(3-acenaphthoyl)-benzoic acid is left as an oil which partially solidifies on cooling in ice. The aqueous solution containing aluminum chloride is decanted through a suction funnel, the residue is washed once with water, and the material collected is returned to the flask. In order to remove traces of aluminum, the acid is dissolved in sodium carbonate solution. This is done by adding 75 ml of 10% sodium carbonate solution and enough water to half fill the flask, and then passing in steam as in a steam distillation until all of the solid material except particles of aluminum oxide or aluminum hydroxide has become dissolved. The solution of the sodium salt of o-(3-acenaphthoyl)-benzoic acid is then cooled well in ice, stirred with 1 g of activated charcoal, filtered by suction, and placed in a 600 ml beaker. The acid is then precipitated by cautious neutralization with hydrochloric acid, adding a little at a time and stirring well. The o-(3-acenaphthoyl)-benzoic acid usually separates as an oil, but it soon solidifies on stirring and cooling. Pure o-(3-acenaphthoyl)-benzoicacid forms colorless, anhydrous crystals melting at 200° C, yield 96%.

Experiments in Organic Chemistry, L. F. Fieser, 188, 1941

IUPAC Name

2-(1,2-dihydroacenaphthylene-5-carbonyl)benzoic acid

InChI

InChI=1S/C20H14O3/c21-19(15-5-1-2-6-17(15)20(22)23)16-11-10-13-9-8-12-4-3-7-14(16)18(12)13/h1-7,10-11H,8-9H2,(H,22,23)

InChI Key

ZEWLGPFHBSBEEG-UHFFFAOYSA-N

Canonical SMILES

C1CC2=CC=CC3=C(C=CC1=C23)C(=O)C4=CC=CC=C4C(=O)O

Depositor-Supplied Synonyms

2-(1,2-dihydroacenaphthylen-5-ylcarbonyl)benzoic acid, 2-(1,2-dihydroacenaphthylene-5-carbonyl)benzoic acid, 4623-31-8, NSC167380, AC1L6QRE, CBMicro_018745, Oprea1_134362, AC1Q723J, SCHEMBL14124755, STOCK1S-94175, CTK1D8857, MolPort-000-629-474, CCG-6494, STL297762, AKOS003611651, MCULE-1666978303, NSC-167380, BIM-0018728.P001, AB00666846-01, AE-848/04969050, 2-(1,2-dihydro-5-acenaphthylenylcarbonyl)benzoic acid, F0051-0015, Benzoicacid, 2-[(1,2-dihydro-5-acenaphthylenyl)carbonyl]-

Removed Synonyms

CID296858

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