Sodium Hydroxide → 4-Benzyloxy-3-methoxy-benzonitrile

HRID 749150ノート

反応式

HRID 749150 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:25]O.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:25])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 755064-(Benzyloxy)-3-methoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

生成物 1

HCID 7937714-Benzyloxy-3-methoxy-benzonitrile収率 80%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4-benzyloxy-3-methoxybenzaldehyde (157 g, 649 mmol), sodium acetate (106 g, 1.29 mol), hydroxylamine hydrochloride (90 g, 1.29 mol) and acetic acid (500 ml) was heated at reflux for 21 hours. The solvent was evaporated and ice/water (1000 ml) was added to the residue forming a sticky solid. The mixture was neutralised with aqueous sodium hydroxide solution then extracted with dichloromethane (2×500 ml). The organic solution was washed with 1.0 N sodium hydroxide (100 ml), brine (100 ml) and then dried over magnesium sulphate. Solvent evaporation in vacuo, trituration of the residue with hexane:ethyl acetate (3:1) and collection of the solid by suction filtration yielded 4-benzyloxy-3-methoxybenzonitrile (123 g, 80% yield) as a brown solid:

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours
  3. customThe solvent was evaporated
  4. additionice/water (1000 ml) was added to the residue
  5. customforming a sticky solid
  6. extractionthen extracted with dichloromethane (2×500 ml)
  7. washThe organic solution was washed with 1.0 N sodium hydroxide (100 ml), brine (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customSolvent evaporation in vacuo, trituration of the residue
  10. customwith hexane:ethyl acetate (3:1) and collection of the solid
  11. filtrationby suction filtration

出典と根拠

ORDレコード
ord-f2169665e72345cc96a1340fd320e72d
出典データセット
uspto-grants-2008_07
特許番号
US07402585B2

反応ノート

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