2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE

In a flask equipped with a mechanical stirrer to the Eaton's reagent prepared from 165.0 g of P4O10 and 840 ml of methanesulfonic acid 144.0 g (ca. 720 mmol) of 3-(naphthalen-2- yl)propanoic acid was added portionwise at room temperature. The formed mixture was stirred overnight, then poured into 2 L of ice-cold water. Crude product was extracted with 3 x 500 ml of dichloromethane. The combined extract was washed with aqueous K2CO3, dried over Na2S04, and then evaporated to dryness. The residue was subjected to flash chromatography using 600 ml of silica gel 60 (40-653 urn) and mixture of hexane and dichloromethane in the ratio 1 :1 as eluent to give 105.0 g (80percent) of the title product as a brownish solid. Anal. calc. for C13H10O: C, 85.69; H, 5.53. Found: C, 85.98; H, 5.75. 1H NMR (CDCIs): 5 9.12 (d, J = 8.5 Hz, 1 H), 7.93 (d, J = 8.3 Hz, 1 H), 7.81 (d, J = 8.1 Hz, 1 H), 7.61 (ddd, J = 8.3 Hz, J = 7.1 Hz, J = 1.2 Hz, 1 H), 7.50 (ddd, J = 8.1 Hz, J = 7.1 Hz, J = 1 .0 Hz, 1 H), 7.39 (d, J = 8.3 Hz, 1 H), 3.12-3.04 (m, 2H), 2.75-2.65 (m, 2H). 13C{1H} NMR (CDCIs): 5207.26, 158.26, 135.47, 132.41 , 130.81 , 129.23, 128.65, 127.90, 126.39, 123.87, 123.76, 36.73, 25.99In a flask equipped with a magnetic stirrer, a solution of naphthalene (50 g, 0.39 mol) in ethylene dichloride (200 mL) was gradually added to a solution of 3-chloropropionylchloride (37. 5 mL, 0.39 mol) and aluminium chloride (65 g) in ethylene dichloride (100 mL) at room temp. After 2 h of stirring at room temperature, the ethylene dichloride layer was poured on 200 g of crushed ice and was extracted with dichioromethane. The combined organic extract was washed by aq K2003 dried on sodium sulphate and filtered. Finally the solvent was evaporated on rota vac under reduced pressure. To the residual oil obtained, concentrated H2S04 (100 mL) was added dropwise, and the mixture was heatedat 900 C for 40 mm. After being cooled to room temperature, the mixture was poured slowly on 500 g of crushed ice and the reaction mixture was extracted with DCM. The combined organic layers were washed with water, saturated aq NaHCO3, brine, dried over Na2SO4, and filtered, and the volatiles were removed in vacuo (43 g, 61percent yield)[0570] 2-Naphthalaldehyde (47 g) and malonic acid (62.4 g) were dissolved in pyridine (300 mL), piperidine (18 mL) was added dropwise thereto, and a reaction was then carried out at 80° C. for 6 hours. After leaving to cool, the reaction mixture was poured into a 1N HCl aqueous solution (1 L), and the crystals thus precipitated were filtered and then recrystallized from methanol, thus giving an unsaturated carboxylic acid (50 g). [0571] A 5percent palladium/activated carbon catalyst (0.5 g) was added to a suspension of the unsaturated carboxylic acid (10 g) thus obtained in tetrahydrofuran (100 mL), hydrogen was added using a rubber balloon at normal pressure (1 atm), and a reaction was carried out for 10 hours. The reaction mixture was filtered using Celite and then concentrated, and the crystals thus obtained was reslurried using a mixed solvent of hexane/ethyl acetate, thus giving a saturated carboxylic acid (7.7 g). [0572] The saturated carboxylic acid (7.6 g) thus obtained was dissolved in methanesulfonic acid (80 mL), and a reaction was carried out at 80° C. for 2 hours. The reaction mixture was poured into water (500 mL), and the crystals thus precipitated were filtered, washed with water, then reslurried with diisopropyl ether, filtered, and dried, thus giving a ketone compound (4.2 g).(a) Neat diacid 8 (5.09 g, 20.8 mmol) was heated to 160

Molecular Weight:182.22
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Exact Mass:182.073164938
Monoisotopic Mass:182.073164938
Topological Polar Surface Area:17.1
Heavy Atom Count:14
Complexity:246
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes