2-[2-Hydroxy-5-(2-methacryloyloxyethyl)phenyl]-2H-benzotriazole → 6-(2H-benzotriazol-2-yl)-4-methacryloyloxyethyl-2-[3'-(2H-benzotriazol-2-yl)-2'-hydroxy-5'-methylphenyl]methylphenol

HRID 2287641Notes

Reaction equation

HRID 2287641 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[N:17]1.[CH3:25][O-:26].[Na+].[CH3:28][OH:29]>C1(C)C(C)=CC=CC=1>[N:17]1[N:16]([C:3]2[C:25]([OH:26])=[C:7]([CH2:2][C:7]3[CH:6]=[C:5]([CH3:8])[CH:4]=[C:3]([N:16]4[N:17]=[C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]5=[N:20]4)[C:28]=3[OH:29])[CH:6]=[C:5]([CH2:8][CH2:9][O:10][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])[CH:4]=2)[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=12

Participants

4

Reactant 2

HCID 7268932-[2-Hydroxy-5-(2-methacryloyloxyethyl)phenyl]-2H-benzotriazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 217088376-(2H-benzotriazol-2-yl)-4-methacryloyloxyethyl-2-[3'-(2H-benzotriazol-2-yl)-2'-hydroxy-5'-methylphenyl]methylphenolYield 70.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ten grams (30.9 mmols) of crude 2-(3'-N,N-diethylaminomethyl-2'-hydroxy-5'-methylphenyl)-2H-benzotriazole obtained following the procedures of Synthesis Example 1 and 10.0 g (30.9 mmols) of 2-(2'-hydroxy-5'-methacryloyloxyethylphenyl)-2H-benzotriazole were dissolved in 64 ml of xylene, and 1.5 ml of a 28% sodium methylate-methanol solution were added thereto. The mixture was then refluxed in a nitrogen stream for 10 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature. Yellow crystals precipitated at this stage were separated through filtration, and recrystallized from chloroform to obtain 12.4 g of 6-(2H-benzotriazol-2-yl)-4-methacryloyloxyethyl-2-[3'-(2H-benzotriazol-2-yl)-2'-hydroxy-5'-methylphenyl]methylphenol (hereinafter abbreviated as "RUVA-1") as white crystals (yield 70.7%, purity 98.6%).

Workup

  1. temperatureThe mixture was then refluxed in a nitrogen stream for 10 hours
  2. customAfter the completion of the reaction
  3. customYellow crystals precipitated at this stage
  4. customwere separated through filtration
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-9bfedfd4b15d41b0b675eea1ee3acb73
Source dataset
uspto-grants-2000_07
Patent number
US06084104

Reaction notes

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