Chloroacetic Acid → 2-(2-(Benzyloxy)ethoxy)acetic acid

HRID 16694

反応式

HRID 16694 の反応式
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][OH:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:15][C:16]([OH:18])=[O:17]>CN(C)C(=O)C>[CH2:3]([O:10][CH2:11][CH2:12][O:13][CH2:15][C:16]([OH:18])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 300Chloroacetic AcidHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydride

生成物 1

HCID 217901362-(2-(Benzyloxy)ethoxy)acetic acid収率 102.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

Sixty % sodium hydride in oil (6.80 g) is suspended in N,N-dimethylacetamide (80 ml) and a solution of 2-(benzyloxy)ethanol (12.9 g) in N,N-dimethylacetamide (50 ml) is added dropwise to the mixture over 10 minutes under ice-cooling. After stirring at room temperature for 15 minutes, the reaction solution is cooled with ice, and thereto is added chloroacetic acid (8.13 g) in small portions. The mixture is then stirred at room temperature for 11 hours. The reaction solution is concentrated under reduced pressure, and to the resulting residue is added aqueous sodium hydrogen carbonate solution and the mixture is washed with diethyl ether. The aqueous layer is acidified with conc. hydrochloric acid, and then extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove solvent under reduced pressure to give [2-(benzyloxy)ethoxy]acetic acid (18.24 g).

後処理

  1. temperaturecooling
  2. temperaturethe reaction solution is cooled with ice
  3. stirringThe mixture is then stirred at room temperature for 11 hours
  4. concentrationThe reaction solution is concentrated under reduced pressure
  5. additionto the resulting residue is added aqueous sodium hydrogen carbonate solution
  6. washthe mixture is washed with diethyl ether
  7. extractionextracted with ethyl acetate
  8. washThe organic layer is washed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. customto remove solvent under reduced pressure

出典と根拠

ORDレコード
ord-7e868632175a4e0181752aefd2fce8ef
出典データセット
uspto-grants-2010_06
特許番号
US07737161B2

関連ノート

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