Sulfuric Acid → chloroacetaldehyde O-tert-butyloxime

HRID 2305080Notes

Reaction equation

HRID 2305080 reaction equation
[Cl:1][CH2:2][CH:3]=[N:4][OH:5].S(=O)(=O)(O)O.[CH2:11]=[C:12]([CH3:14])[CH3:13].C(=O)([O-])O.[Na+]>C(OCC)C>[C:12]([O:5][N:4]=[CH:3][CH2:2][Cl:1])([CH3:14])([CH3:13])[CH3:11]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 57350373N-(2-Chloroethylidene)hydroxylamine

Product 1

HCID 53697151chloroacetaldehyde O-tert-butyloxime

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Then, 0.47 g of chloroacetoaldehyde oxime, 0.1 ml of concentrated sulfuric acid, and 10 ml of diethyl ether are placed in a reaction vessel, into which isobutene gas is blown with stirring under ice cooling, and the stirring is further continued at room temperature. After completion of the reaction, the reaction mixture is slowly poured into saturated aqueous sodium hydrogencarbonate solution, and extracted twice with diethyl ether. The diethyl ether layers are combined, washed with 10% aqueous sodium hydroxide solution and water in this order, dried over anhydrous magnesium sulfate, and concentrated, which affords chloroacetoaldehyde O-tert-butyloxime.

Workup

  1. customis further continued at room temperature
  2. customAfter completion of the reaction
  3. extractionextracted twice with diethyl ether
  4. washwashed with 10% aqueous sodium hydroxide solution and water in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-54bc228858bc4204918f6d7c05d500c2
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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