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

HRID 1276851
Notes
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Reaction equation

HRID 1276851 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-925cd206f84042c7b9c7a8bc1536159d
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06166218

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes