1,2-Dibromoethane → 1-(3-Chloro-2-methylphenyl)cyclohexanol

HRID 249462

반응식

HRID 249462 반응식
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

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 7967CyclohexanoneHCID 83682,6-Dichlorotoluene

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b33c2528f031498c8ad5385a6c7670fc
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05214187

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