HCID 135970814, compound → 2-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenol

HRID 582275Notes

Reaction equation

HRID 582275 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[N+:20]([O-])=O)[CH:5]=1>[OH-].[Na+].[Zn]>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]2=[N:12][N:11]([C:6]3[CH:5]=[C:4]([CH2:3][CH2:2][OH:1])[CH:9]=[CH:8][C:7]=3[OH:10])[N:20]=[C:14]2[CH:15]=1

Participants

4

Reactant 1

HCID 135970814HCID 135970814, compound

Product 1

HCID 544779472-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenolYield 77.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 14798Sodium HydroxideSolvent2×

Procedure

5.91 g (18 mmols) of crude 4-(2-hydroxyethyl)-2-[(4-chloro-2-nitrophenyl)azo]phenol synthesized in Example 4 was dissolved in 18 ml of aqueous solution of 2N sodium hydroxide. Subsequently, 9 ml of previously prepared aqueous solution of 25% sodium hydroxide and 5.4 g (83 mmols) of zinc powder were simultaneously added over a period of about 3 hours. The subsequent treatment was carried out in the same manner as in Example 6, giving 4.02 g of 2-(5-chloro-2H-benzotriazole-2-yl)-4-(2-hydroxyethyl)phenol as pale yellow crystals (yield 68%, purity 88%).

Sources & evidence

ORD record
ord-40e65e3b6d5d4552a0fbd28c96dbf402
Source dataset
uspto-grants-1999_07
Patent number
US05922882

Reaction notes

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