Acetic Anhydride → N-(4-benzyloxybenzyl)acetohydroxamic acid

HRID 1087637

反応式

HRID 1087637 の反応式
[Na].[CH2:2]([O:9][C:10]1[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CO.C(OCC)(=O)C.O>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]([C:19](=[O:21])[CH3:20])[OH:16])=[CH:17][CH:18]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

9

反応物 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 7633594-Benzyloxy-benzaldehyde oximeHCID 5360545Sodium

生成物 1

HCID 129265N-(4-benzyloxybenzyl)acetohydroxamic acid

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium cyanoborohydrodide (21.3 g) was added in portions to a solution of 4-benzyloxybenzaldehyde oxime (51 g) in acetic acid (250 ml) at ca 50° (cooling). After the reduction was complete, acetic anhydride (22.5 ml) was added in one portion, and the mixture was stirred for 1 hour. The mixture was then poured into water, and the neutral product was isolated with ethyl acetate. The residue was treated with potassium carbonate (2 g) in methanol (400 ml) to hydrolyse the O-acetyl material, then the solvent was evaporated. Addition of 20% citric acid solution (400 ml) and isolation with ethyl acetate furnished N-(4-Benzyloxybenzyl)acetohydroxamic acid (32 g), m.pt. 119°-120° [from ethyl acetate-light petroleum (b.p.t. 60°-80°)].

後処理

  1. temperature(cooling)
  2. customthe solvent was evaporated
  3. additionAddition of 20% citric acid solution (400 ml) and isolation with ethyl acetate

出典と根拠

ORDレコード
ord-a4ae16462e7b4a2b8baee55a51aa65c2
出典データセット
uspto-grants-1991_07
特許番号
US05036157

関連ノート

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