反応 #2045044

ord-e1fdf190586b47d2bdae6094ee54b428

反応方程式

COC(=O)COCCBr
(2-bromoethoxy)acetic acid methyl ester
O=[N+]([O-])c1ccc(O)cc1
4-nitrophenol
O=C([O-])[O-].[K+].[K+]
K2CO3
[I-].[Na+]
sodium iodide
COC(=O)COCCOc1ccc([N+](=O)[O-])cc1
59
収率 43.6%
COC(=O)COCCOc1ccc([N+](=O)[O-])cc1
[2-(4-Nitrophenoxy)ethoxy]acetic acid methyl ester
収率 43.6%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度refluxed for 24 hours
  2. 2
    workup.DISTILLATIONAcetone was distilled off
  3. 3
    workup.ADDITIONwater (100 ml) was added
  4. 4
    ろ過Crude 59 was filtered
  5. 5
    その他dried
  6. 6
    その他purified by column chromatography on silica gel

実験手順

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 59 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 59 (4 g, 43.6%) as a white fluffy powder. M.p: 96-97.8° C.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08409559B2uspto-grants-2013_04