3-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methyl-2-propenoate → HCID 21708848, compound

HRID 651552Notes

Reaction equation

HRID 651552 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])=[CH:4][C:3]=1[N:17]1[N:21]=[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]2=[N:18]1.[CH3:26][O-:27].[Na+].CO>C1(C)C(C)=CC=CC=1>[N:18]1[N:17]([C:3]2[C:2]([OH:1])=[C:7]([CH2:2][C:7]3[CH:6]=[C:5]([CH3:8])[CH:4]=[C:3]([N:17]4[N:18]=[C:19]5[CH:25]=[CH:24][CH:23]=[CH:22][C:20]5=[N:21]4)[C:26]=3[OH:27])[CH:6]=[C:5]([CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])[CH:4]=2)[N:21]=[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=12

Participants

4

Reactant 2

HCID 220350653-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]propyl 2-methyl-2-propenoateHCID 23694274Sodium methanolate methanol

Product 1

HCID 21708848HCID 21708848, compoundYield 71%

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 10.5 g (31.1 mmols) of 2-(2′-hydroxy-5′-methacryloyloxypropylphenyl)-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 point were separated through filtration, and recrystallized from chloroform to obtain 12.8 g of 6-(2H-benzotriazol-2-yl)-4-methacryloyloxypropyl-2-[3′-(2H-benzotriazol-2-yl)-2′-hydroxy-5′-methylphenyl]methylphenol (hereinafter abbreviated as “RUVA-3”) as white crystals (yield 71.0%, 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 point
  4. customwere separated through filtration
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-8345c004bde04e5b950804e3579c53bf
Source dataset
uspto-grants-2001_08
Patent number
US06281313B1

Reaction notes

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