O-Butylhydroxylamine Hydrochloride → Methyl 2-[3-(1-n-butoxyiminoethyl)phenoxymethyl]phenylglyoxylate O-methyloxime

HRID 374307Notes

Reaction equation

HRID 374307 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=O)[CH3:24])[CH:18]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.[CH2:27]([O:31][NH2:32])[CH2:28][CH2:29][CH3:30]>CO>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[N:32][O:31][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:24])[CH:18]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 12283956O-Butylhydroxylamine HydrochlorideHCID 54262751methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloxime

Product 1

HCID 54150028Methyl 2-[3-(1-n-butoxyiminoethyl)phenoxymethyl]phenylglyoxylate O-methyloximeYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.8 g (0.017 mol) of methyl 2-(3-acetylphenoxymethyl)phenylglyoxylate O-methyloxime and 2.5 g (0.020 mol) of n-butoxyamine hydrochloride in 60 ml of methanol are stirred at room temperature for 24 hours. The mixture is then hydrolyzed with water and extracted with methyl tert-butyl ether. The organic phase is washed with water, dried and concentrated. 5.0 g (71%) of the title compound are obtained as a colorless oil (compound no. 470).

Workup

  1. extractionhydrolyzed with water and extracted with methyl tert-butyl ether
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9427cbd491d94832bde5c416a83ce9d1
Source dataset
uspto-grants-1992_11
Patent number
US05166399

Reaction notes

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