Isopropanol → 8-Hydroxy-6-oxo-octanoic acid methyl ester

HRID 1063475ノート

反応式

HRID 1063475 の反応式
Cl[O-].[Na+].[CH3:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([OH:15])[CH2:12][CH2:13][OH:14].C(O)(C)C>C(O)(=O)C>[CH3:4][O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][C:11](=[O:15])[CH2:12][CH2:13][OH:14]

参加物

5

反応物 3

HCID 3776IsopropanolHCID 113559606,8-Dihydroxyoctanoic acid methyl esterHCID 23665760Sodium Hypochlorite

生成物 1

HCID 120390238-Hydroxy-6-oxo-octanoic acid methyl ester収率 80%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

100 ml of aqueous sodium hypochlorite solution (10-13% active chlorine) were added dropwise at room temperature, over a period of 45 minutes, to 16.6 g (87 mmol) of 6,8-dihydroxyoctanoic acid methyl ester in 200 ml of glacial acetic acid. After stirring for a further 3 hours at room temperature, 180 ml of isopropanol were added in order to destroy excess sodium hypochlorite, and stirring was carried out for 10 minutes. The reaction mixture was then added to 1200 ml of water and extracted several times with methylene chloride. The combined organic phases were washed with cold-saturated sodium hydrogen carbonate solution. After drying over sodium sulfate, the solvent was distilled off using a rotary evaporator. 13.0 g (80%) of 8-hydroxy-6-oxo-octanoic acid methyl ester were obtained.

後処理

  1. customto destroy excess sodium hypochlorite
  2. stirringstirring
  3. waitwas carried out for 10 minutes
  4. additionThe reaction mixture was then added to 1200 ml of water
  5. extractionextracted several times with methylene chloride
  6. washThe combined organic phases were washed with cold-saturated sodium hydrogen carbonate solution
  7. dry with materialAfter drying over sodium sulfate
  8. distillationthe solvent was distilled off
  9. customa rotary evaporator

出典と根拠

ORDレコード
ord-5e1eb68fcf904fbb9bbf7f375608a741
出典データセット
uspto-grants-2005_11
特許番号
US06965029B2

反応ノート

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