Hydrochloric Acid → methyl E-2-hydroxyimino-2-(3-phenoxylphenyl)acetate

HRID 584354

反応式

HRID 584354 の反応式
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:4]#N.[OH-:19].[K+].[CH2:21]([OH:23])C.Cl>O>[OH:1]/[N:2]=[C:3](/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)\[C:4]([O:23][CH3:21])=[O:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 853082792-Hydroxyimino-2-(3-phenoxyphenyl)acetonitrile

生成物 1

HCID 86589771methyl E-2-hydroxyimino-2-(3-phenoxylphenyl)acetate収率 33%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2-hydroxyimino-2-(3-phenoxyphenyl)acetonitrile (3.00 g), potassium hydroxide (3.40 g), ethanol (15 ml) and water (15 ml) was heated under reflux for 24 hours. The reaction mixture was acidified with 1 N HCl, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The reaction mixture was dissolved in methanol (30 ml), admixed with concentrated sulfuric acid (a catalytic amount), and then heated under reflux for 24 hours. The reaction mixture was combined with aqueous sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain methyl Z-2-hydroxyimino-2-(3-phenoxyphenyl)acetate (1.14 g, yield 33%) as an oil from a fraction eluted with ethyl acetate-hexane (1:2, v/v).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe reaction mixture was dissolved in methanol (30 ml), admixed with concentrated sulfuric acid (a catalytic amount), and
  8. temperaturethen heated
  9. temperatureunder reflux for 24 hours
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-7bb1114c885f461894b889c96aa45221
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

関連ノート

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