4-Nitrophenol → Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate

HRID 638714노트

반응식

HRID 638714 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[CH3:19][O:20][C:21](=[O:27])[CH2:22][O:23][CH2:24][CH2:25]Br>CC(C)=O>[CH3:19][O:20][C:21](=[O:27])[CH2:22][O:23][CH2:24][CH2:25][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18946503Methyl (2-bromoethoxy)acetate

생성물 1

HCID 59253929Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate수율 43.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a mixture of 4-nitrophenol (5 g, 36 mmol), anhydrous K2CO3 (20 g, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy) acetic acid methyl ester (11 g, 56 mmol) and refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 22 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 22 (4 g, 43.6%) as a white fluffy powder. The melting point was found to be 96-97.8° C. The structure was confirmed with IR and NMR.

후처리

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (100 ml) was added
  4. filtrationCrude 22 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-a64f066403194fab90fa2237b478c377
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691364B2

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