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Formic Acid → 5-Benzenesulfonyl-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole

HRID 990198
Notes
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Reaction equation

HRID 990198 reaction equation
[C:1]1([S:7][C:8]2[CH:40]=[CH:39][C:11]3=[N:12][N:13]([C:15]4[CH:20]=[C:19]([C:21]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)([CH3:31])[CH3:30])[C:16]=4[OH:38])[N:14]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C(C)=CC=CC=1.C(O)=[O:50].OO.[OH2:54]>O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[C:1]1([S:7]([C:8]2[CH:40]=[CH:39][C:11]3=[N:12][N:13]([C:15]4[CH:20]=[C:19]([C:21]([CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:23])[CH3:22])[CH:18]=[C:17]([C:29]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)([CH3:30])[CH3:31])[C:16]=4[OH:38])[N:14]=[C:10]3[CH:9]=2)(=[O:50])=[O:54])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 7237O-Xylene2×HCID 186728375-phenylthio-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole

Product 1

HCID 22034021
5-Benzenesulfonyl-2-(2-hydroxy-3-alpha-cumyl-5-tert-octylphenyl)-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 150191Sodium Tungstate DihydrateCatalyst

Conditions

Temperature
50 °C

Procedure

A 1000 mL flask is charged with 75.2 g of 5-phenylthio-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole, prepared in Example 4, 102 g of xylene, 0.9 g of sodium tungstate dihydrate and 18.4 g of formic acid. The mixture is heated to 50° C. To this stirred mixture is slowly added 36.3 g of 50% hydrogen peroxide so that the temperature does not exceed 85° C. Additional xylene and water are then added. The organic layer is separated, washed with aqueous sodium sulfite, then twice with water and concentrated. The crude product residue is recrystallized from methanol to yield 75.2 g of the title compound as a light yellow solid melting at 170-171° C.

Workup

  1. customdoes not exceed 85° C
  2. customThe organic layer is separated
  3. washwashed with aqueous sodium sulfite
  4. concentrationtwice with water and concentrated
  5. customThe crude product residue is recrystallized from methanol

Sources & evidence

ORD record
ord-d7e79fe91fc448469450eae3b7e18986
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06458872B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes