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

HRID 1506086ノート

反応式

HRID 1506086 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 53574309,10-Epoxy-1,5-cyclododecadiene収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bd5ee9578c584e5ebf5a3275113174a0
出典データセット
uspto-grants-2015_12
特許番号
US09217122B2

反応ノート

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