4-Nitrophenol → 4-(2-Hydroxy-1-decyloxy)nitrobenzene

HRID 645323

反応式

HRID 645323 の反応式
[Na].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].C1(C)C=CC=CC=1.[O:19]1[CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20]1>O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[OH:19][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][O:11][C:8]1[CH:9]=[CH:10][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 9804-NitrophenolHCID 1140TolueneHCID 169931,2-EpoxydecaneHCID 5360545Sodium

生成物 1

HCID 222377694-(2-Hydroxy-1-decyloxy)nitrobenzene収率 388.6%

試薬・触媒・溶媒 2

HCID 11433187Bis(tetrabutylammonium) sulphate触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

The sodium salt of 4-nitrophenol (28.19 g, 0.175 mol) was dissolved in water (50 mL) and toluene (300 mL) and tetrabutylammonium sulfate (6.0 g) was added. 1,2-Epoxydecane (27.3 g, 0.175 mol) was added to this mixture and the reaction was heated at 100° C. for 5 days. The toluene layer was separated and washed with water (4×75 mL), 1N hydrochloric acid (2×75 mL) and water (75 mL). The organic layer was dried over sodium sulfate, filtered and the solvent removed. The crude product was purified by silica gel chromatography (2-3% methanol/methylene chloride) to afford 4-(2-hydroxy-1-decyloxy)nitrobenzene as a pale oil (20 g, 0.68 mol, 39% yield).

後処理

  1. customThe toluene layer was separated
  2. washwashed with water (4×75 mL), 1N hydrochloric acid (2×75 mL) and water (75 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe crude product was purified by silica gel chromatography (2-3% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-81dbb5e70efa4827874fde291b252acd
出典データセット
uspto-grants-2010_04
特許番号
US07704667B2

関連ノート

読み込み中…