6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

General procedure: 6-Hydroxy-1-tetralone (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing KGeneral procedure: 6-Hydroxy-1-tetralone (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane. 6-(Benzyloxy)-3, 4-dihydronaphthalen-1(2H)-one (6a) The title compound was prepared in a yield of 97percent: mp 100.9–102.1 °C (cyclohexane). 1H NMR (BrukerAvance III 600, CDCl3) δ 2.09 (p, J = 6.5 Hz, 2H), 2.56 – 2.61 (m, 2H), 2.90 (t, J = 6.1 Hz, 2H), 5.09 (s, 2H), 6.77 (d, J = 2.2 Hz, 1H), 6.88 (dd, J = 8.7, 2.6 Hz, 1H), 7.30 – 7.36 (m, 1H), 7.36 – 7.43 (m, 4H), 8.00 (d, J = 8.7 Hz, 1H); 13C NMR (Bruker Avance III 600, CDCl3) δ 23.29, 30.10, 38.85, 69.20, 113.53, 113.58, 122.11, 126.64, 128.99, 129.67, 131.78, 135.20, 146.94, 162.30, 197.08; APCI-HRMS m/z: calcdfor C17H17O2 (MH+), 253.1223, found 253.1220.Step 1: Step 1: The mixture of 6-hydroxy-3, 4-dihydro-2H-naphthalen-l-one (30.74 g, 0.1895 mol), benzyl bromide (27.0 mL, 0.227 mol) and potassium carbonate (39.3 g, 0.284 mol) in acetone (250 mL, 3.4 mol) was heated to reflux under an atmosphere of nitrogen for 3 hours. The mixture was cooled to 10 °C with an ice bath, filtered and washed with small amount of acetone. The filtrate was concentrated in rotavap. The resulting crystals were collected by filtration and washed with EtOAc-hexane then hexane to give a pale yellow solid product as the first crop. The mother liquid was concentrated in rotavapor and the residue was purified by chromatograph with EtOAc:hexane (0:100 to 20:80) to give the second crop of solid product (38.07g, 80percent). To a solution of 6-hydroxy-3, 4-dihydronaphthalen-1(2H)-one (CAS registry number: 3470-50-6) (24.3 g) inacetone (160 mL), benzyl bromide (29.4 mL) and potassium carbonate (31.1 g) were added at room temperature andthe mixture was stirred at 40°C for 3.5 hours. After insoluble matters were filtered off, the mixture was concentrated andwashed with a mixed solvent of tert-butyl methyl ether (MTBE)-hexane (1 : 4) to give the title compound (34.5 g) havingthe following physical property.TLC: Rf 0.38 (hexane : ethyl acetate = 3 : 1).

Molecular Weight:252.31
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:252.115029749
Monoisotopic Mass:252.115029749
Topological Polar Surface Area:26.3
Heavy Atom Count:19
Complexity:306
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes