1-(4-Methoxy-1-naphthyl)ethanone

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 540, 1971 DOI: 10.1021/jo00803a011
Tetrahedron Letters, 31, p. 3933, 1990 DOI: 10.1016/S0040-4039(00)97510-5

Synthesis

Aluminum trichloride (800 mg, 6 mmol) in anhydrous dichloromethane (12 mL) was cooled to 0 °C under nitrogen protection and acetyl chloride (236 mg, 3 mmol) was slowly added. The reaction mixture was stirred at room temperature for 10 min before 1-methoxynaphthalene (474 mg, 3 mmol) was added and stirring was continued at room temperature overnight. After completion of the reaction, the reaction was quenched with water, the organic phase was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether=1:15, v/v) to afford 4-methoxynaphthaleneacetophenone (338 mg, 56% yield) as a white solid.1H NMR (300 MHz, CDCl3) δ: 9.01-9.96 (m, 1H), 8.32-8.35 (m, 1H), 8.03 (d, 1H), 7.63-7.65 (m, 1H), 7.53-7.58 (m, 1H), 6.79 (d, 1H), 4.07 (s, 3H), 2.72 (s, 3H).LC-MS: m/z 201 [M+1]+.

References

[1] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[2] Patent: US2012/220629, 2012, A1. Location in patent: Page/Page column 46
[3] Patent: WO2012/113103, 2012, A1. Location in patent: Page/Page column 62-63
[4] Recueil des Travaux Chimiques des Pays-Bas, 1945, vol. 64, p. 214,216
[5] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 402,407