Dodecanal → N,N-didodecylhydroxylamine

HRID 1885412Notes

Reaction equation

HRID 1885412 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl.[NH2:15][OH:16]>CO.C(OCC)(=O)C.[Pt]>[CH2:1]([N:15]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 2

HCID 8194DodecanalHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 9864141N,N-didodecylhydroxylamineYield 51%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of dodecanal (9.2 g, 50 mmol) and hydroxylamine hydrochloride (3.8 g, 54 mmol) in 75 ml of methanol and 10 ml of ethyl acetate is shaken under hydrogen at 40-45 psi (2.8-3.15 Kg/cm2) for five hours at room temperature in the presence of a catalytic amount of 5% platinum on carbon (450 mg). The reaction mixture is then filtered through CELITE filter agent. The filtrate is concentrated and the residue is treated with a saturated aqueous potassium carbonate solution till the pH is over 10. A white solid is isolated by filtration and is recrystallized from methanol to provide 4.7 g (51% yield) of the title compound as a white solid melting at 88° C.

Workup

  1. filtrationThe reaction mixture is then filtered through CELITE
  2. filtrationfilter agent
  3. concentrationThe filtrate is concentrated
  4. additionthe residue is treated with a saturated aqueous potassium carbonate solution till the pH
  5. customA white solid is isolated by filtration
  6. customis recrystallized from methanol

Sources & evidence

ORD record
ord-23bd21f5e1a94142b19fe8d6398b23d3
Source dataset
uspto-grants-1992_09
Patent number
US05144075

Reaction notes

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