m-Chloroperbenzoic acid → 9,10-Epoxy-1,5-cyclododecadiene

HRID 1506086노트

반응식

HRID 1506086 반응식
[CH:1]1=[CH:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12]1.C(=O)(O)[O-:14].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH:1]12[O:14][CH:12]1[CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]2

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86718830E,E,E-1,4,8-cyclododecatriene

생성물 1

HCID 53574309,10-Epoxy-1,5-cyclododecadiene수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a mechanically stirred solution of E,E,E-1,4,8-cyclododecatriene (22.5 g, 139 mmol, available commercially from Alfa Aesar) in methylene chloride (200 ml) was added sodium bicarbonate (12 g, 139 mmol). The mixture was cooled to 0° C. and m-chloroperbenzoic acid (24 g, 166 mmol) was added in small portions over 2 hours. The reaction mixture was stirred at 0° C. for 1 hour, then allowed to warm to ambient temperature. Filtration, washing with sodium hydrogen sulphate (2 portions of 30 ml 10% aq. solution) and distillation of the methylene chloride solvent yielded the crude product. The crude product was dissolved in MTBE, washed with aqueous NaHCO3, water and brine. The solvent was evaporated and the product (31.3 g; 30% starting material, 63% monoepoxide; 7% diepoxide) purified by distillation. The pure monoepoxide crystallised spontaneously (yield=79% taking into account recovered substrate).

후처리

  1. temperatureto warm to ambient temperature
  2. filtrationFiltration
  3. washwashing with sodium hydrogen sulphate (2 portions of 30 ml 10% aq. solution) and distillation of the methylene chloride solvent

출처 및 근거

ORD 기록
ord-bd5ee9578c584e5ebf5a3275113174a0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09217122B2

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