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

HRID 1058101Notes

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 tide 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-533d20c3763c448fbe332f2d94de571f
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515051B2

Reaction notes

Loading…