Hydrogen Bromide → alpha-Phenoxy propionaldehyde oxime

HRID 65487Notes

Reaction equation

HRID 65487 reaction equation
[CH:1](=[N:4][OH:5])[CH2:2][CH3:3].BrBr.BrC(=NO)CC.[O-:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+].Br>C(Cl)(Cl)(Cl)Cl>[O:14]([CH:2]([CH3:3])[CH:1]=[N:4][OH:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 24408BromineHCID 641641Propionaldehyde oximeHCID 4445035Phenolate Sodium2×HCID 734321831-Bromo-propionaldehyde oxime

Product 1

HCID 86741044alpha-Phenoxy propionaldehyde oxime

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Using the procedure of Example I, propionaldehyde oxime in carbon tetrachloride is brominated with bromine introduced at -5° to 0° C. To the resulting solution of 1-bromo-propionaldehyde oxime is added dropwise with stirring a suspension of sodium phenoxide in carbon tetrachloride. The reaction is allowed to go to completion and any residual sodium phenoxide is neutralized with hydrogen bromide gas. The precipitated sodium bromide is collected by filtration, and the filtrate concentrated under reduced pressure to provide the desired α-phenoxy propionaldehyde oxime.

Workup

  1. additionintroduced at -5° to 0° C
  2. filtrationThe precipitated sodium bromide is collected by filtration
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-cac7a746ad3b4282b052d07942965292
Source dataset
uspto-grants-1986_09
Patent number
US04614813

Reaction notes

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