Hydroxyamine hydrochloride → 2-Hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime

HRID 1709998Notes

Reaction equation

HRID 1709998 reaction equation
[OH:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:16][OH:17].C(=O)(O)[O-].[Na+]>C(O)C.O.O1CCCC1>[OH:1][C:2]1[C:9]([Br:10])=[CH:8][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:3]=1[CH:4]=[N:16][OH:17]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 71720963-Bromo-5-tert-butyl-2-hydroxybenzaldehyde

Product 1

HCID 1363645842-Hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oximeYield 157%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 12.86 g (50.0 mmol) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde (see L. C. Felton and J. H. Brewer, Science, 105:409 (1947) as an example of how to obtain this material) and 3.82 g (55.0 mmol) of hydroxylamine hydrochloride in 30 ml of ethanol, 30 ml of water and 30 ml of tetrahydrofuran was cooled in an ice-water bath. Sodium bicarbonate (5.04 g, 60.0 mmol) was added in small portions over 15 minutes. After stirring for 1 hour at ambient temperature, water (200 ml) was added and the solid was filtered and dried. There was obtained 13.2 g (78.5 mmol, 97%) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime as a white solid; mp 167.5°-168° C.

Workup

  1. temperaturewas cooled in an ice-water bath
  2. filtrationthe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-1863b5d413ee427fbba1d405c5cb822a
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

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