반응 #42594

반응 방정식

oxone

methyl sulfide

4-[(methylthio)methyl]cyclohexanecarboxylic acid

sodium bicarbonate

acetone

→

4-[(methylsulfonyl)methyl]cyclohexanecarboxylic acid

수율 90.8%

용매

EDTA

sodium hydroxide

반응 조건

후처리

1. 1
   기타quenched with sodium bisulfite
2. 2
   추출extracted with ethyl acetate (3×100 mL)
3. 3
   세척The combined organic layers were washed with water
4. 4
   건조dried (sodium sulfate)
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure

실험 절차

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).

출처