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

HRID 83809ノート

反応式

HRID 83809 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of 4-nitrophenol (5 g, 36 mmol), anhydrous K2CO3 (20 g, 145 mmol) and sodium iodide (2 g, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy)acetic acid methyl ester (11 g, 56 mmol) and then refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 42 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 42 (4 g, 43.6%) as a white fluffy powder with an m.p. between 96-97.8° C.

後処理

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (100 ml) was added
  4. filtrationCrude 42 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-e88b722b9c5f489cad5f6b16a4ac40bf
出典データセット
uspto-grants-2014_09
特許番号
US08846845B2

反応ノート

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