Benzaldehyde, 4-(phenylmethoxy)- → HCID 73444829, compound

HRID 1003680Notes

Reaction equation

HRID 1003680 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([NH:21][OH:22])([CH3:20])([CH3:19])[CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[N+:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[O-:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 98586N-tert-butylhydroxylamineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 73444829HCID 73444829, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-benzyloxybenzaldehyde, N-tert-butylhydroxylamine and catalytic amount of p-toluenesulfonic acid monohydrate in benzene was refluxed under argon atmosphere with a Dean-Stark trap to remove generated water. The mixture was then rotary evaporated to give a residue which was purified by recrystallization. The title compound was obtained in 89.3% yield as a white powder, m.p. 111.0° C. (Rf =0.66 on a silica gel plate using EtOAc as an eluant).

Workup

  1. temperaturewas refluxed under argon atmosphere with a Dean-Stark trap
  2. customto remove
  3. customThe mixture was then rotary evaporated
  4. customto give a residue which
  5. customwas purified by recrystallization

Sources & evidence

ORD record
ord-711763e15b8f4a2dad8aa81b397c6492
Source dataset
uspto-grants-2000_04
Patent number
US06046232

Reaction notes

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