Anisole → 1,4-Bis(4-methoxyphenyl)butan-1-one

Participants

Reaction Steps

The crude acid chloride (2.07 g, 9.7 mmol) and anisole (1.26 g, 11.6 mmol) were dissolved in 1,2-dichloroethane (32 mL) and chilled in an ice bath. The mixture was treated with aluminum chloride (3.9 g, 29.1 mmol) in portions, stirred for 5 minutes, then mixed with ice water (50 mL). The mixture was extracted with dichloromethane (3×10 mL), and the extracts were combined, washed with saturated sodium chloride (100 mL), dried (MgSO4), then concentrated under reduced pressure. The residue was flushed through silica gel with 10:1 hexane/ethyl acetate then concentrated to give 1,4-bis-(4-methoxyphenyl)butan-1-one (2.49 g, 82%). 1H NMR (400 MHz, CDCl3): 7.90 (d, J=8.8 Hz, 2H), 7.11 (d, J=8.4 Hz, 2H), 6.91 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 3.86 (s, 3H), 3.78 (s, 3H), 2.90 (t, J=7.3 Hz, 2H), 2.65 (t, J=7.7 Hz, 2H), 2.02 (m, 2H) ppm. IR (NaCl): 1674, 1602, 1244 cm-1.

Provenance & Evidence