Anisole → HCID 13427164, compound

Participants

Reaction Steps

2-Thiophenylacetyl chloride (12.38 g, 77.1 mmol) in CH2Cl2 (40 ml) was added to a solution of anisole (8.33 g, 77.1 mmol) and AlCl3 (10.3 g, 77.1 mmol) in CH2Cl2 (200 ml) at room temperature. The reaction was completed after 2 hours, and the mixture was poured over a 10% HCl/ice slurry. The organic layer was washed with H2O and brine, dried over MgSO4, and the solvent was removed under reduced pressure. The crude solid was chromatographed on SiO2 (1 kg) eluting with CH2Cl2 /Hexane, 3/1, to afford 23 (9.37 g, 52.4%), m.p. 44.0°-45.5° C. and the ortho isomer (2.14 g, 12%)

Provenance & Evidence