Hydroquinone → 2-[2-Hydroxy-5-(2-methacryloyloxyethyl)phenyl]-2H-benzotriazole

HRID 370747Notes

Reaction equation

HRID 370747 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[N:11]1[N:15]=[C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]2=[N:12]1.[C:20](O)(=[O:24])[C:21]([CH3:23])=[CH2:22].C1(C=CC(O)=CC=1)O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:20](=[O:24])[C:21]([CH3:23])=[CH2:22])=[CH:4][C:3]=1[N:11]1[N:15]=[C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]2=[N:12]1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 688251Benzeneethanol, 3-(2H-benzotriazol-2-yl)-4-hydroxy-

Product 1

HCID 7268932-[2-Hydroxy-5-(2-methacryloyloxyethyl)phenyl]-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2'-Hydroxy-5'-hydroxyethylphenyl)-2H-benzotriazole (150 g, 0.59 mol), methacrylic acid (55 ml, 0.65 mol), hydroquinone (2.4 g), p-toluenesulfonic acid monohydrate (3 g) and toluene (2 l) were placed in a 3 liter flask equipped with a Dean and Stark receiver. After 1.5 hours of refluxing the mixture, another 2.7 g of p-toluenesolfonic acid monohydrate was added and the refluxing was continued for another 15.5 hours. Approximately 10 ml of water was collected (theoretical: 10.6 g) and the yield of the desired compound was 93.7% as judged by a gas chromatography. Another 1 g of p-toluenesolfonic acid monohydrate was added and the reflusing was continued for another 3 hours. A yield of 95.6% was shown by a gas chromatography. After cooling the reaction mixture, it was washed with aqueous sodium hydrogen carbonate solution, water, 5% hydrochloric acid and water. The organic layer was dried with anhydrons magnesium sulfate and chromatographed through an alumina (Fisher, 80-200 mesh) column. After evaporation of the solvent, the residue was recrystallized from distilled methanol twice. Yield: 141.8 g (74%); Purity: >99.9% (G.C.). The IR and NMR data were consistent with the structure.

Workup

  1. customequipped with a Dean and Stark receiver
  2. temperatureAfter 1.5 hours of refluxing the mixture
  3. customApproximately 10 ml of water was collected (theoretical: 10.6 g)
  4. additionAnother 1 g of p-toluenesolfonic acid monohydrate was added
  5. waitthe reflusing was continued for another 3 hours
  6. temperatureAfter cooling the reaction mixture, it
  7. washwas washed with aqueous sodium hydrogen carbonate solution, water, 5% hydrochloric acid and water
  8. dry with materialThe organic layer was dried with anhydrons magnesium sulfate
  9. customchromatographed through an alumina (Fisher, 80-200 mesh) column
  10. customAfter evaporation of the solvent
  11. customthe residue was recrystallized
  12. distillationfrom distilled methanol twice

Sources & evidence

ORD record
ord-f31e11f2bb614fe7919d9c8b545074b4
Source dataset
uspto-grants-1985_07
Patent number
US04528311

Reaction notes

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