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

HRID 1276851Notes

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

Participants

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

customdoes not exceed 85° C
customThe organic layer is separated
washwashed with aqueous sodium sulfite
concentrationtwice with water and concentrated
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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