Sodium Hydroxide → HCID 136348391, compound

HRID 869402Notes

Reaction equation

HRID 869402 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=O.Cl.[NH2:13][OH:14].[OH-].[Na+]>CCO>[Br:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[N:13][OH:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 156059702-Bromo-3,6-dihydroxybenzaldehyde

Product 1

HCID 136348391HCID 136348391, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-bromo-3,6-dihydroxy-benzaldehyde (12A) (50 g, 0.23 mol) and hydroxylamine hydrochloride (19.2 g, 0.28 mol) was added 95% EtOH (500 mL), followed by NaOH (13.8 g, 0.345 mol). The reaction mixture was stirred at room temperature for 2 hours, then extracted with ethyl acetate and concentrated to give 2-bromo-3,6-dihydroxy-benzaldehyde oxime (12B) (45 g, 84.1% yield) as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-670e5e37d68044959b9b8a514109aa0e
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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