Sulfuric Acid → allyl 3-(5-chloro-2H-benzotriazole-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy-benzene propanate

HRID 1779527

Reaction equation

HRID 1779527 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2=[N:6][N:7]([C:9]3[CH:10]=[C:11]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH2:26][CH2:27]CCCCC)=[O:23])[CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=3[OH:15])[N:8]=[C:4]2[CH:3]=1.S(=O)(=O)(O)O>C(O)C=C>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2=[N:6][N:7]([C:9]3[CH:10]=[C:11]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH:12]=[C:13]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:14]=3[OH:15])[N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 174297Octyl 5-tert-butyl-3-(5-chloro-2H-benzotriazole-2-yl)-4-hydroxybenzenepropionate

Product 1

HCID 20764418allyl 3-(5-chloro-2H-benzotriazole-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy-benzene propanateYield 90%

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Procedure

220 g (0.45 mol) of octyl 3-(5-chloro-2H-benzotriazole-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy-benzene propanate manufactured by CIBA GEIGY INC. under the trade name of "TINUVIN 109" were dissolved in 500 ml of allyl alcohol, and was admixed with 5 ml of concentrated sulfuric acid. The resulting solution was refluxed for five hours. After cooling, a precipitated product was filtered off. The resulting solid substance was dissolved in 300 ml of methylene chloride, washed with a saturated aqueous solution of NaHCO3 and dried over magnesium sulfate. After filtration, the solvent was distilled off and the resulting solid substance was recrystallized from hexane to produce allyl 3-(5-chloro-2H-benzotriazole-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy-benzene propanate, referred to hereinafter as a precursor (4) at a yield of 90%.

Workup

  1. temperatureThe resulting solution was refluxed for five hours
  2. temperatureAfter cooling
  3. filtrationa precipitated product was filtered off
  4. dissolutionThe resulting solid substance was dissolved in 300 ml of methylene chloride
  5. washwashed with a saturated aqueous solution of NaHCO3
  6. dry with materialdried over magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off
  9. customthe resulting solid substance was recrystallized from hexane

Sources & evidence

ORD record
ord-bbfc0c79f8424822a073d8cf55863fcf
Source dataset
uspto-grants-1997_05
Patent number
US05627227

Linked notes

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