Aluminum(III) Chloride → 2'-Cyclohexyl-5'-hydroxy-4'-methoxyacetophenone

Participants

Reaction Conditions

Reaction Steps

A solution of ketone 52 (50 mg, 0.172 mmol) in dry CH2Cl2 (1.5 mL) was treated with AlCl3 (0.069 mg, 0.517 mmol) and the resulting mixture stirred magnetically at 18° C. under a nitrogen atmosphere for 2.5 h then partitioned between H2O (10 mL) and CH2Cl2 (10 mL). The separated aqueous phase was extracted with CH2Cl2 (1×10 mL) and the combined organic fractions dried (MgSO4), filtered and concentrated, under reduced pressure, onto TLC-grade silica (ca. 80 mg). The resulting free-flowing solid was subjected to flash chromatography (1:19→15:85 v/v ethyl acetate/hexane gradient elution) to afford the title compound 53 (31 mg, 72%) as a colourless oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence