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

HRID 444174

反応式

HRID 444174 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6a6f3fd7760e41baa196c10fefa12708
出典データセット
uspto-grants-1981_04
特許番号
US04263219

関連ノート

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