Ethanol → 2-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime

HRID 1710002Notes

Reaction equation

HRID 1710002 reaction equation
[OH:1][C:2]1[C:9]([Br:10])=[C:8]([Cl:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:17][OH:18].C(O)C.C(=O)(O)[O-].[Na+]>O1CCCC1.O>[OH:1][C:2]1[C:9]([Br:10])=[C:8]([Cl:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:3]=1[CH:4]=[N:17][OH:18]

Participants

7

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 230354152-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde

Product 1

HCID 1364045082-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oximeYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.25 g (7.72 mmol) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde and 0.59 g (8.49 mmol) of hydroxylamine hydrochloride in 15 ml of 1:1:1 tetrahydrofuran:ethanol:water was cooled in an ice-water bath. Sodium bicarbonate (0.78 g, 9.26 mmol) was added in small portions over 15 minutes. After stirring overnight at ambient temperature, water (25 ml) was added and the solid was filtered and dried. There was obtained 2.00 g (6.52 mmol, 85%) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime as a white solid after crystallization from cyclohexane mp 175°-177° C.

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-0a0e0be3a83846a4a00ecb16d29a45ac
Source dataset
uspto-grants-1990_08
Patent number
US04952583

Reaction notes

Loading…