Acetone → 4-[(Methylsulfonyl)methyl]cyclohexanecarboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl sulfide from step 5 (100 mg, 0.5 mmol) in sodium hydroxide solution (1.5 mL, 0.5 M solution in water) was added sodium bicarbonate (360 mg, 4.3 mmol) and acetone (1 mL) followed by the addition of a solution of oxone (430 mg, 0.7 mmol) in 0.0004 M EDTA (2 mL). The reaction mixture was stirred at room temperature for 2 h and then quenched with sodium bisulfite. The reaction mixture was acidified with 1 N hydrochloric acid and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide 4-[(methylsulfonyl)methyl]cyclohexanecarboxylic acid (100 mg): 1H NMR (300 MHz, CD3OD) δ 3.11–3.08 (m, 2H), 2.96 (s, 3H), 2.53–2.51 (m, 1H), 2.18–2.16 (m, 1H), 1.99–1.93 (m, 2H), 1.79–1.25 (m, 6H).

Provenance & Evidence