1-(2-naphthyl)propan-1-one synthesis

8synthesis methods

Product Name:1-(2-naphthyl)propan-1-one
CAS Number:6315-96-4
Molecular formula:C13H12O
Molecular Weight:184.23

91-20-3 Synthesis

91-20-3
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$14.00/25g

79-03-8 Synthesis

79-03-8
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$9.00/1g

6315-96-4
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Yield:6315-96-4 98%

Reaction Conditions:

with aluminum (III) chloride in 1,2-dichloro-ethane at 35; for 4 h;

Steps:

1-(2-Naphthyl)propanone (12). To a solution of propionyl chloride 11 (5.1 g, 55 mmol) and aluminum chloride (7.7 g, 58 mmol) in 1,2-dichloroethane (16 mL) was added dropwise a solution of naphthalene 10 (7.9 g, 62 mmol) in 1,2-dichloroethane (16 mL) over 3 h at 35° C. and it was allowed to stir for 1 h. The reaction was added 3MHCl solution at 0° C. and then separated a white solid. The filtrate was washed with water. The organic layer was dried over Na₂SO₄and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish compound 12 (9.9 g, 98%) as a colorless oil, R_f=0.56 (hexane:EtOAc=9:1). ¹H NMR (300 MHz, CDCl₃): δ 8.58 (d, 1H, J=8.7 Hz), 7.94 (d, 1H, J=8.1 Hz), 7.86-7.80 (m, 2H), 7.59-7.42 (m, 3H), 3.04 (q, 2H, J=6.9 Hz), 1.27 (t, 3H, J=6.9 Hz). ¹³C NMR (75 MHz, CDCl₃): δ 205.2, 136.0, 133.8, 132.2, 130.0, 128.3, 127.7, 127.1, 126.3, 125.7, 124.3, 35.2, 8.56. MS (EI): m/z 184.15 [M]⁺. HRMS (EI), calcd for C₁₃H₁₂O 184.0888, found [M]⁺ 184.0890.