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

HRID 645323

반응식

HRID 645323 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 222377694-(2-Hydroxy-1-decyloxy)nitrobenzene수율 388.6%

시약·촉매·용매 2

HCID 11433187Bis(tetrabutylammonium) sulphate촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-81dbb5e70efa4827874fde291b252acd
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704667B2

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