Didodecylamine → N,N-didodecyl-2-hydroxy-3,4,6-trimethylbenzamide

HRID 364664Notes

Reaction equation

C1(O[C:8](=[O:19])[C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[C:11]([CH3:17])[C:10]=2[OH:18])C=CC=CC=1.[CH2:20]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH2:33]([N:32]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8](=[O:19])[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[C:11]([CH3:17])[C:10]=1[OH:18])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

Reactant 2

HCID 18157Didodecylamine

HCID 137651872-Hydroxy-3,4,6-trimethylbenzoic acid phenylester

Product 1

HCID 13765188N,N-didodecyl-2-hydroxy-3,4,6-trimethylbenzamideYield 91%

Conditions

Temperature: 120 °C

Procedure

In a 250 ml flask fitted with a mechanical stirrer and a reflux condenser, were placed 30.7 g (0.12 mole) of the 2-hydroxy-3,4,6-trimethylbenzoic acid phenyl ester prepared in step (2) and 42.36 g (0.12 mole) of didodecylamine. This mixture was heated in a nitrogen atmosphere at 120° C. for 12 hours. The phenol formed was distilled off under vacuum (7 g were thus collected). After cooling, the crystallization of the desired product was started by scraping.

Workup

customIn a 250 ml flask fitted with a mechanical stirrer and a reflux condenser

Sources & evidence

ORD record: ord-7f0619fd15b94fafbd992dd3c7ac2623
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605697

Reaction notes

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