Water → (Z)-4-(benzyloxy)benzaldehyde oxime

HRID 75841

Reaction equation

HRID 75841 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.Cl.[NH2:18][OH:19].O>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[N:18]\[OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 5403280(Z)-4-(benzyloxy)benzaldehyde oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-(benzyloxy)benzaldehyde (12.9 g) in MeOH (129 ml), Hydroxylamine hydrochloride (6.34 g) was added and the reaction mixture was refluxed for 3 hours and then cooled. The reaction mixture was concentrated to obtain pale brown residue. To this residue, water was added and it was extracted with EtOAc. Organic layer was collected, dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized from DCM-Petroleum ether to obtain the title compound as white solid. Yield: 11.5 g (83%); 1HNMR (DMSO-d6; 300 MHz): δ 10.98 (s, 1H), 8.06 (s, 1H), 7.53 (d, 2H), 7.33-7.46 (m, 5H), 7.05 (d, 2H), 5.13 (s, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. concentrationThe reaction mixture was concentrated
  4. customto obtain pale brown residue
  5. extractionit was extracted with EtOAc
  6. customOrganic layer was collected
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto obtain off white solid, which
  10. customwas crystallized from DCM-Petroleum ether

Sources & evidence

ORD record
ord-ff81819fa333498ba651c556493f880f
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

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