HRID278510

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7500

Ethylbenzene

C8H10

结构：CC(C)(C)c1cc2c(c(C(C)(C)C)c1)OC(=O)C2O

HCID6850821

未命名化合物

2 次

PRODUCTS

生成物

结构：CCc1cccc(C2C(=O)Oc3c2cc(C(C)(C)C)cc3C(C)(C)C)c1

HCID22628566

未命名化合物

收率 5.6%

结构：CCc1ccccc1C1C(=O)Oc2c1cc(C(C)(C)C)cc2C(C)(C)C

HCID22628573

未命名化合物

收率 1.3%

HCID86752879

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

PROCEDURE

实验过程

To a solution of 262.3 g (1.00 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example la) in 500 ml (4.08 mol) of ethyl benzene are added 40 g of Fulcat 22B and the mixture is refluxed for 1.5 hours on a water separator. The Fulcat 22B catalyst is then removed by filtration and excess ethyl benzene is removed by distillation on a vacuum rotary evaporator. GC-MS analysis shows the residue to consist of a mixture of 59.2% of the para-isomer (compound (105). Table 1), 10.8% of the meta-isomer (compound (105A) and 21.1% of the ortho-isomer(compound (105B). Crystallisation of the residue from 400 ml of methanol yields 163.8 g (47%) of 5,7-di-tert-butyl)-3-(4-ethylphenyl)-3H-benzofuran-2-one (compound (105), Table 1) (para-isomer), which additionally contains 5.6% of the meta-isomer 5,7-di-tert-butyl-3-(3-ethylphenyl)-3H-benzofuran-2-one (compound (105A) and 1.3% of the ortho-isomer 5,7-di-tert-butyl-3-(2-ethylphenyl)3H-benzofuran-2-one (compound (105B). Further crystallisation from methanol yields the almost pure para-isomer (compound (105), Table 1), m.p. 127-132° C. In accordance with the general procedure desdcribed in this Example, compounds (102), (106), (107), (114), (115), (116), (117), (118) and (119) are prepared from 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example 1a) and the corresponding aromatic hydrocarbons, typically including m-xylene, isopropylbenzene (cumene), tert-butylbenzene, biphenyl, thiophene, p-xylene, dibenzofuran, phenanthrene and diphenyl ether. To prepare compound (119), 2 equivalents of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one are used starting from diphenyl ether.

WORKUP

后处理

customThe Fulcat 22B catalyst is then removed by filtration and excess ethyl benzene
customis removed by distillation on a vacuum rotary evaporator
additionto consist of a mixture of 59.2% of the para-isomer (compound (105). Table 1), 10.8% of the meta-isomer (compound (105A) and 21.1% of the ortho-isomer(compound (105B)
customCrystallisation of the residue from 400 ml of methanol

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-508484b5a880481aa41af5f9d788e89d
来源数据集: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06359148B1
来源说明: uspto-grants-2002_03

反应 SMILES

[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21]>O>[CH2:20]([C:22]1[CH:27]=[CH:26][C:25]([CH:10]2[C:9]3[CH:15]=[CH:5][CH:6]=[CH:7][C:8]=3[O:12][C:11]2=[O:13])=[CH:24][CH:23]=1)[CH3:21].[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:17])[CH3:18])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([CH2:20][CH3:21])[CH:23]=3)[C:9]=2[CH:15]=1)([CH3:2])([CH3:3])[CH3:4].[C:16]([C:7]1[CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[C:15]2[O:12][C:11](=[O:13])[CH:10]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:20][CH3:21])[C:9]=2[CH:8]=1)([CH3:19])([CH3:18])[CH3:17]