Water → 1-(4-Methoxyphenyl)-2-phenylbutan-1-one

Participants

Reaction Conditions

Reaction Steps

2-Phenylbutyryl chloride (50.0 mL, 299 mmol) was dissolved in anisole (75 mL) and cooled to 0° C. AlCl3 (40.377 g, 303 mmol) was added portionwise and the resulting mixture allowed to warm to RT then stirred for 2 h. Ice was added portionwise followed by H2O (100 mL). The mixture was extracted with CH2Cl2 (3×100 mL) and the combined organics dried (MgSO4) and concentrated. The residue was distilled to remove the remaining anisole (1 mm Hg, 40-55° C.) to provide 2 (77.27 g, 100%) as a tan oil. 1H NMR (400 MHz, CDCl3): δ 0.90 (t, J=7.5 Hz, 3H), 1.85 (dq, 1H), 2.18 (dq, 1H), 3.81 (s, 3H), 4.40 (t, J=7.2 Hz, 1H), 6.85 (d, J=5.0 Hz, 2H), 7.19 (m, 1H), 7.28 (m, 4H), 7.95 (d, J=5.0 Hz, 2H).

Provenance & Evidence