p-Toluenesulfonic acid → 5-Phenylthio-2-[2-hydroxy-3-tert-butyl-5-(beta-octyloxycarbonylethyl)phenyl]-2H-benzotriazole

HRID 440189Notes

Reaction equation

HRID 440189 reaction equation
[C:1]1([S:7][C:8]2[CH:32]=[CH:31][C:11]3=[N:12][N:13]([C:15]4[CH:16]=[C:17]([CH:23]=[C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]=4[OH:26])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[N:14]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:44]1([CH3:51])[C:45]([CH3:50])=[CH:46][CH:47]=[CH:48][CH:49]=1>C(OCC)(=O)C>[C:1]1([S:7][C:8]2[CH:32]=[CH:31][C:11]3=[N:12][N:13]([C:15]4[CH:16]=[C:17]([CH2:18][CH2:19][C:20]([O:22][CH2:50][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:44][CH3:51])=[O:21])[CH:23]=[C:24]([C:27]([CH3:29])([CH3:28])[CH3:30])[C:25]=4[OH:26])[N:14]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7237O-XyleneHCID 212181283-(5-phenylthio-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamic acid

Product 1

HCID 212181325-Phenylthio-2-[2-hydroxy-3-tert-butyl-5-(beta-octyloxycarbonylethyl)phenyl]-2H-benzotriazoleYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Likewise, to a 250 mL round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet, condenser, and a Dean-Stark trap are charged 4.3 g (0.0096 mol) of 3-(5-phenylthio-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamic acid, 3.4 g (0.026 mol) of Exxel 8, an isomeric mixture of octanols available from Exxon Chemicals, 70 mg of p-toluenesulfonic acid, and 20 mL of xylene. The mixture is refluxed 3.5 hours, is cooled to room temperature, and a portion of ethyl acetate is added. The solution is washed once with water, twice with saturated sodium bicarbonate solution, and once with brine. After drying over anhydrous magnesium sulfate, the solvent is removed under reduced pressure to afford 5.17 g (96% yield) of the title compound as a viscous yellow oil. Analysis by nmr (CDCl3) is consistent with the structure of the title compound.

Workup

  1. customLikewise, to a 250 mL round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet, condenser
  2. temperatureThe mixture is refluxed 3.5 hours
  3. washThe solution is washed once with water, twice with saturated sodium bicarbonate solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-831a9699a74c4bbba7d4b1ab755e233c
Source dataset
uspto-grants-1996_05
Patent number
US05516914

Reaction notes

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