Hydrogen Peroxide → Dodecyl 2-hydroxy-4-(methylsulfinyl)butanoate

HRID 1754040노트

반응식

HRID 1754040 반응식
[OH:1][CH:2]([CH2:18][CH2:19][S:20][CH3:21])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:4].[OH:22]O>CO>[OH:1][CH:2]([CH2:18][CH2:19][S:20]([CH3:21])=[O:22])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:4]

참가 물질

4

반응물 2

HCID 784Hydrogen PeroxideHCID 86689971Dodecyl 2-hydroxy-4-(methylthio)butanoate

생성물 1

HCID 86689972Dodecyl 2-hydroxy-4-(methylsulfinyl)butanoate수율 98.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of dodecyl 2-hydroxy-4-(methylthio)butanoate (20 g, 62.8 mmol) in methanol (100 mL) was added 30% hydrogen peroxide (20.0 mL, 176 mmol) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for about 3 hrs. The reaction was mildly exothermic. Analysis indicated the reaction was completed within two hours. Water (400 mL) was added to the mixture. The mixture was extracted with EtOAc (2×100 mL). The extracts were combined and washed with a 10% sodium bisulfite solution (100 mL). The organic phase was dried with anhydrous magnesium sulfate and the solvent was evaporated with a rotary evaporator. A colorless viscous liquid was obtained which solidified upon standing to give a white solid (20.6 g, 98%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.86 (t, J=6.83 Hz, 3 H) 1.20-1.34 (m, 18 H) 1.53-1.62 (m, 2 H) 1.81-1.92 (m, 1 H) 1.98-2.07 (m, 1 H) 2.53 (d, J=4.13 Hz, 3 H) 2.60-2.90 (m, 2 H) 3.99-4.11 (m, 2 H) 4.12-4.19 (m, 1 H) 5.63 (dd, J=5.88, 2.38 Hz, 1 H). m/z 335 (MH+).

후처리

  1. customThe ice bath was removed
  2. waitwas completed within two hours
  3. additionWater (400 mL) was added to the mixture
  4. extractionThe mixture was extracted with EtOAc (2×100 mL)
  5. washwashed with a 10% sodium bisulfite solution (100 mL)
  6. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated with a rotary evaporator
  8. customA colorless viscous liquid was obtained which

출처 및 근거

ORD 기록
ord-400aec320c1d440992db8cb1212d9a9e
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169203B2

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