CYCLOPENTYL 4-THIOMETHYLPHENYL KETONE synthesis

Yield: 93%

Reaction Conditions:

aluminium trichloride in chloroform;water

Steps:

21.1 Step 1
Step 1 Cyclopentyl-(4-(methylthio)phenyl)methanone To a suspension of anhydrous aluminum chloride (9.3 g, 69.6 mmol) in 58 mL CHCl₃ at 0° C. was added dropwise cyclopentanecarbonyl chloride (10.0 g, 75.4 mmol), followed by thioanisole (7.21 g, 58.0 mmol). The ice bath was removed and the mixture was stirred at room temperature for 2 h. Water (200 ml) was added with cooling, the layers were separated and the aqueous layer was extracted with CHCl₃ (3*50 mL). The combined aqueous layers were dried over MgSO₄, filtered and concentrated. The residue was chromatographed on silica gel (4% EtOAc/hexane) to give 11.9 g of the title ketone (93%). ¹ H NMR (CD₃ COCD₃) δ 7.94 (d, 2H), 7.36 (d, 2H), 3.79 (q, 1H), 2.56 (s, 3H), 2.00-1.71 (m, 4H), 1.70-1.50 (m, 4H).

References:

Merck Frosst Canada, Inc. US5981576, 1999, A