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

HRID 1110889Notes

Reaction equation

HRID 1110889 reaction equation
C([BH3-])#N.[Na+].[CH2:5]([O:12][C:13]1[CH:21]=[CH:20][C:16]([CH:17]=[N:18][OH:19])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.CO.C(OCC)(=O)C.O>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]([C:22](=[O:24])[CH3:23])[OH:19])=[CH:20][CH:21]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 7633594-Benzyloxy-benzaldehyde oximeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 129265N-(4-benzyloxybenzyl)acetohydroxamic acid

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium cyanoborohydride (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.pt. 60°-80°)].

Workup

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

Sources & evidence

ORD record
ord-750634e29e37466aa2583813e115d5be
Source dataset
uspto-grants-1990_12
Patent number
US04977188

Reaction notes

Loading…