HRID1650042

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID962

Water

H2O

HCID6410

tert-Butyl hydroperoxide

C4H10O2

HCID9266

Cyclooctane

C8H16

结构：CC1(C)CC(OC(=O)CCCCCCCCC(=O)OC2CC(C)(C)NC(C)(C)C2)CC(C)(C)N1

HCID164282

Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate

C28H52N2O4

PRODUCTS

生成物

结构：CC1(C)CC(OC(=O)CCCCCCCCC(=O)OC2CC(C)(C)N(OC3CCCCCCC3)C(C)(C)C2)CC(C)(C)N1OC1CCCCCCC1

HCID19768323

未命名化合物

收率 68%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID14802

Molybdenum trioxide

MoO3

CONDITIONS

反应条件

温度: 118 °C

PROCEDURE

实验过程

A mixture of 75 g (156 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 1.3 g of molybdenum trioxide and 475 ml of cyclooctane is heated to 118° C. To this mixture is added 130 g (1.01 mol) of 70% aqueous tert-butyl hydroperoxide during a 5-hour period. The reaction mixture is maintained at reflux during the addition period, and water is collected in a Dean-Stark trap. The red reaction mixture is heated at reflux for 7 hours after the addition is complete to discharge the red color. The solids are removed by filtration and the filtrate is evaporated to give a yellow oil. Purification (Waters Prep 500A HPLC, 20:1 hexane:ethyl acetate) affords 78.7 g (68% yield) of the title compound as a colorless syrup.

WORKUP

后处理

temperatureThe reaction mixture is maintained
customis collected in a Dean-Stark trap
customThe red reaction mixture
temperatureis heated
temperatureat reflux for 7 hours
additionafter the addition
customThe solids are removed by filtration
customthe filtrate is evaporated
customto give a yellow oil
customPurification (Waters Prep 500A HPLC, 20:1 hexane:ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ce854cc29184450f89d68e088062edd6
来源数据集: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04921962
来源说明: uspto-grants-1990_05

反应 SMILES

[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[NH:28][C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:20])([CH3:19])[NH:16][C:15]([CH3:22])([CH3:21])[CH2:14]1)=[O:11].[CH2:35]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[C:43]([O:47]O)(C)([CH3:45])[CH3:44].[OH2:49]>[Mo](=O)(=O)=O>[C:1]([O:24][CH:25]1[CH2:30][C:29]([CH3:32])([CH3:31])[N:28]([O:47][CH:43]2[CH2:45][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:44]2)[C:27]([CH3:34])([CH3:33])[CH2:26]1)(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:18][C:17]([CH3:19])([CH3:20])[N:16]([O:49][CH:35]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[C:15]([CH3:21])([CH3:22])[CH2:14]1)=[O:11]