Hydroxylamine → N-hydroxyhexadecanamide

HRID 1658409Notes

Reaction equation

HRID 1658409 reaction equation
[C:1]([O:18]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:21][OH:22].[Na].OC1C=CC2C(=CC=CC=2)N=1>C(O)C>[C:1]([NH:21][OH:22])(=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 12366Ethyl palmitateHCID 5360545SodiumHCID 178515546HCID 178515546, compound

Product 1

HCID 414280N-hydroxyhexadecanamideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.2 g. of ethyl palmitate and 2 g. of hydroxylamine are reacted at room temperature in 300 ml. of ethanol in the presence of 1.7 g. of the sodium salt of 2-hydroxyquinoline. The reaction is complete in 5 hours, and 11.7 g. of palmitohydroxamic acid are obtained (yield: 85%), m.p. 100° - 101°C. after recrystallization from ethanol-petroleum ether(1:1).

Sources & evidence

ORD record
ord-63aedffb4a784800a57e2bbca8be9c28
Source dataset
uspto-grants-1976_06
Patent number
US03963728

Reaction notes

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