Water → Benzaldehyde, 5-chloro-2-hydroxy-, oxime

HRID 1587800Notes

Reaction equation

HRID 1587800 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=O.Cl.[NH2:18][OH:19].O>C(O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=[N:18][OH:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 124815-Chloro-salicylaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 177640Benzaldehyde, 5-chloro-2-hydroxy-, oximeYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridine (20 ml) was added to a stirred suspension of 5-chloro-2-hydroxybenzaldehyde (5.0 g) and hydroxylamine hydrochloride (2.77 g) in ethanol (20 ml) and stirring was continued for 18 hours. The mixture was then added to water (150 ml) and extracted with ether (3×50 ml). The combined extracts were washed with water (2×50 ml), dried (MgSO4) and concentrated to give a yellow oil which slowly crystallised on standing. The solid was collected by filtration and washed with hexane to give 5-chloro-2-hydroxybenzaldoxime (4.25 g) as white crystals, m.p. 125°-126° C.; NMR: 6.91(1H,d,J=8 Hz), 7.15(1H,d,J=2.5 Hz), 7.22(1H,dd,J=8,2.5 Hz); 7.55(1H,b), 8.16(1H,s), 9.26(1H,b).

Workup

  1. extractionextracted with ether (3×50 ml)
  2. washThe combined extracts were washed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a yellow oil which
  6. customslowly crystallised
  7. filtrationThe solid was collected by filtration
  8. washwashed with hexane

Sources & evidence

ORD record
ord-0fa4f119000944f1b77ca521aa6043f5
Source dataset
uspto-grants-1993_06
Patent number
US05219874

Reaction notes

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