Triethylamine → 2-(2'-Hydroxy-5'-methyacrylyloxypropyl-3'-tert-butylphenyl)-5-chloro-2H-benzotriazole

HRID 370746Notes

Reaction equation

[C:1](Cl)(=[O:5])[C:2](C)=[CH2:3].[CH2:7](N(CC)CC)C.[OH:14][C:15]1[C:20]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][C:18]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:17][C:16]=1[N:29]1[N:33]=[C:32]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:31]2=[N:30]1>C(Cl)Cl>[OH:14][C:15]1[C:20]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][C:18]([CH2:25][CH2:26][CH2:27][O:28][C:1](=[O:5])[CH:2]=[CH:3][CH3:7])=[CH:17][C:16]=1[N:29]1[N:33]=[C:32]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:31]2=[N:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methacrylyl chloride (5.9 ml) and triethylamine (8.5 ml) were added dropwise at -5° C. to a solution of 2-(2'-hydroxy-5'-hydroxypropyl-3'-tert-butylphenyl)-5-chloro-2H-benzotriazole (20 g) in 250 ml of methylene chloride. The reaction mixture was stirred at 0° C. overnight and then washed with 1N hydrochloric acid and water. The methylene chloride solution of the product was dried with sodium sulfate, passed through alumina column and evaporated. The crude yield of the product was 22 g (90%). A polymerization grade sample was obtained by recrystallization from methanol--methylene chloride mixture, m.p. 74.5°-76.5° C.

Workup

washwashed with 1N hydrochloric acid and water
dry with materialThe methylene chloride solution of the product was dried with sodium sulfate
customevaporated
customA polymerization grade sample was obtained by recrystallization from methanol

Sources & evidence

ORD record: ord-3fddfb3bb0af460ab14b8550a51723cd
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528311

Reaction notes

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