Toluene → 2,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

HRID 2082170Notes

Reaction equation

HRID 2082170 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]=[N:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:14]=1[OH:27])([O-])=O.C1(C)C=CC=CC=1.CC(O)CC.C(N(CCCC)CCCC)CCC>[C].[Pd].O>[OH:27][C:14]1[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:18][C:13]=1[N:12]1[N:11]=[C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]2=[N:1]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6568(+-)-2-ButanolHCID 7622TributylamineHCID 104112Phenol, 2-(2-(4-chloro-2-nitrophenyl)diazenyl)-4,6-bis(1,1-dimethylethyl)-

Product 1

HCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenolYield 78.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

39.0 g (0.1 mol) of 2-nitro-4-chloro-2'-hydroxy-3',5'-di-t-butylazobenzene, 0.125 g of 5% palladium carbon, 100 ml of toluene, 60 ml of 2-butanol, 120 ml of water and 7 g of tributylamine were charged into a 500-ml stainless autoclave with an agitator. Reaction was effected in the same manner as that employed in Example 1. After the reaction had been completed, after treatment was performed in the same way as that employed in Example 1 to obtain 28.1 g of 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorbenzotriazole(yield, 78.6%; melting point, 152° to 153° C.).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-ee668654c7394118aef8cf47221195d3
Source dataset
uspto-grants-1993_02
Patent number
US05187289

Reaction notes

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