O-Xylene → 2-(Lauramido)ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate

HRID 1659897Notes

Reaction equation

[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:18]([C:22]1[CH:23]=[C:24]([CH2:33][CH2:34][C:35](O)=[O:36])[CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])([CH3:21])([CH3:20])[CH3:19].C1(C)C(C)=CC=CC=1>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4].O>[C:29]([C:26]1[CH:25]=[C:24]([CH2:33][CH2:34][C:35]([O:1][CH2:2][CH2:3][NH:4][C:5](=[O:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:36])[CH:23]=[C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])[C:27]=1[OH:28])([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of 13.9 g (0.055 mole) N-(2-hydroxyethyl)lauramide, 13.9 g (0.05 mole) 3(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 0.5 g Tyzor TBT catalyst and 100 ml xylene was refluxed until evolution of water ceased (3 hours). The xylene was removed by vacuum stripping. The residue was taken up in acetonitrile. White crystals separated upon cooling at about -10° C. The acetonitrile was decanted and the recrystallization was repeated. The last traces of acetonitrile were removed under vacuum, and the title product thus obtained was a yellow oil at room temperature.

Workup

custom(3 hours)
customThe xylene was removed by vacuum stripping
customWhite crystals separated
customThe acetonitrile was decanted
customthe recrystallization
customThe last traces of acetonitrile were removed under vacuum

Sources & evidence

ORD record: ord-b3ff0b9801c74ba8b367eef2ae104c85
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04305868

Reaction notes

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