Diethyl Ether → Ethyl dodecane hydroximate

HRID 67945

Reaction equation

HRID 67945 reaction equation
[Cl-].O[NH3+].CC[O:6]CC.[CH2:9]([O:11][C:12](=[NH:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:10]>O>[C:12](=[N:24][OH:6])([O:11][CH2:9][CH3:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21645Hydroxylamine HClHCID 3442835Ethyldodecaneimidate

Product 1

HCID 86738559Ethyl dodecane hydroximateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2 °C

Procedure

A mixture containing fourteen grams of hydroxylammonium chloride dissolved in 100 ml of water was added to 100 ml of ether in a 250 ml flask. The resulting mixture was cooled to 2° C. and 45.4 g of ethyldodecaneimidate were added to the mixture with stirring. The reaction mixture was stirred for an additional 30 minutes at 2° C. The layers were separated and the aqueous layer was extracted three times with 75 ml of ether. The ether layer and washings were combined and then dried over sodium sulfate and concentrated to yield 37.3 g (77% yield) of ethyl dodecane hydroximate as a white, solid substance. IR and NMR analyses confirmed the structure.

Workup

  1. stirringThe reaction mixture was stirred for an additional 30 minutes at 2° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted three times with 75 ml of ether
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e15a47277379479ea60e7f0627918e63
Source dataset
uspto-grants-1982_08
Patent number
US04347342

Linked notes

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