Chloroacetaldehyde → chloroacetaldehyde O-tert-butyloxime

Reaction equation

[Cl:1][CH2:2][CH:3]=O.Cl.[C:6]([O:10][NH2:11])([CH3:9])([CH3:8])[CH3:7]>>[C:6]([O:10][N:11]=[CH:3][CH2:2][Cl:1])([CH3:9])([CH3:8])[CH3:7]

Participants

Reactant 2

HCID 33Chloroacetaldehyde

HCID 2777906O-tert-butylhydroxylamine hydrochloride

Product 1

HCID 53697151chloroacetaldehyde O-tert-butyloximeYield 94%

Procedure

To 9.81 g of 40% aqueous chloroacetaldehyde solution was added 3.77 g of O-tert-butylhydroxylamine hydrochloride with stirring at room temperature. After stirring at room temperature for 2 hours, the reaction mixture was extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated, which afforded 4.21 g (yield, 94%) of chloroacetaldehyde O-tert-butyloxime, nD23.2 1.4418.

Workup

stirringAfter stirring at room temperature for 2 hours
extractionthe reaction mixture was extracted twice with diethyl ether
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b2b0155c5f504200a2b0561866f2596b
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448444B1

Reaction notes

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