1-Chloro-4-nitrobenzene → 1-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene

HRID 444174

반응식

HRID 444174 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=1)([O-:13])=[O:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:17]2[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 952944-Methylphenethyl alcohol

생성물 1

HCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene수율 80.1%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

A mixture of 2-(4-methylphenyl)ethyl alcohol (VIII) (13.6 g, 0.1 mole), 4-nitrochlorobenzene (IX: X=Cl) (15.8 g, 0.1 mole), toluene (92 g), tetra-n-butylammonium bromide (3.2 g, 0.01 mole) and a 50% aqueous sodium hydroxide solution (24 g) was stirred vigorously at 50° to 60° C. for 5 hours. The organic layer was separated, washed with water two times and then concentrated in vacuo. By recrystallizing the crude product from 95% ethanol, 20.6 g (yield, 80%) of 4-[2-(4-methylphenyl)ethoxy]nitrobenzene (VI) were obtained as white crystals.

후처리

  1. customThe organic layer was separated
  2. washwashed with water two times
  3. concentrationconcentrated in vacuo
  4. customBy recrystallizing the crude product from 95% ethanol

출처 및 근거

ORD 기록
ord-6a6f3fd7760e41baa196c10fefa12708
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04263219

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