Dodecanal → N,N-didodecylhydroxylamine

HRID 1885413Notes

Reaction equation

HRID 1885413 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].[Pt]=O>[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

7

Reactant 2

HCID 8194DodecanalHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 9864141N,N-didodecylhydroxylamineYield 50%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of dodecanal (9.2 g, 50 mmol) and hydroxylamine hydrochloride (2.0 g, 29 mmol) in 70 ml of methanol and 10 ml of ethyl acetate is shaken under hydrogen at 40-45 psi (2.8-3.15 Kg/cm2) for 2.5 hours at room temperature in the presence of a catalytic amount of 5% platinum on carbon (400 mg) and platinum oxide (15 mg). The reaction mixture is then worked up as described in Example 4 to give, after recrystallization from methanol, 4.6 g (50% yield) of the title compound as a white solid identical to that prepared in Example 4.

Workup

  1. customto give

Sources & evidence

ORD record
ord-b5650a363ad34f629448917d2390db68
Source dataset
uspto-grants-1992_09
Patent number
US05144075

Reaction notes

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