1,2-二溴乙烷 → 1-(3-Chloro-2-methylphenyl)cyclohexanol

HRID 249462

反应方程式

HRID 249462 反应方程式
BrCCBr.Cl[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH3:13].[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1>[Cl:12][C:8]1[C:7]([CH3:13])=[C:6]([C:14]2([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=1

参与物

5

反应物 3

HCID 78391,2-二溴乙烷HCID 7967环己酮HCID 83682,6-二氯甲苯

产物 1

HCID 145554331-(3-Chloro-2-methylphenyl)cyclohexanol

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂3 次

实验过程

96 g (4 moles) of Mg turnings in 60 ml of absolute tetrahydrofuran (THF) are initially taken under a nitrogen atmosphere. 1 ml of 1,2-dibromoethane is added at 65° C., after which a solution of 644 g (4 moles) of 2,6-dichlorotoluene in 1.5 1 of absolute THF is added dropwise in the course of 21/4 hours. Thereafter, the mixture is stirred for 4 hours under reflux and cooled to room temperature, and 352.8 g (3.6 moles) of cyclohexanone in 250 ml of absolute THF are added under nitrogen. When the reaction is complete, the Grignard reaction mixture is worked up in an aqueous medium in a conventional manner and the solvent is substantially removed by distillation under reduced pressure. The residue is subjected to incipient distillation (30°-107° C./0.27 mbar). The remaining crude product (676 g), which contains as much as 90% of 1-(3'-chloro-2'-methylphenyl)-cyclohexanol, can be further purified by column chromatography using toluene as the mobile phase.

后处理

  1. temperatureunder reflux
  2. customthe Grignard reaction mixture
  3. customthe solvent is substantially removed by distillation under reduced pressure
  4. distillationThe residue is subjected to incipient distillation (30°-107° C./0.27 mbar)
  5. customcan be further purified by column chromatography

来源与证据

ORD记录
ord-b33c2528f031498c8ad5385a6c7670fc
来源数据集
uspto-grants-1993_05
专利号
US05214187

关联笔记

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