Sodium Hydroxide → 3,3'-bis-(2H-benzotriazol-2-yl)-5,5'-di-tert-butyl-1,1'-biphenyl-2,2'-diol

HRID 1699107Notes

Reaction equation

HRID 1699107 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]2[C:23]([OH:43])=[C:24]([N:32]=[N:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N+:40]([O-])=O)[CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=2)[C:13]=1[OH:44])([O-])=O.[OH-].[Na+]>[Zn].C(O)C>[N:1]1[N:11]([C:12]2[CH:17]=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:15]=[C:14]([C:22]3[C:23]([OH:43])=[C:24]([N:32]4[N:40]=[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]5=[N:33]4)[CH:25]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:27]=3)[C:13]=2[OH:44])[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1356276103,3'-Bis-(2-nitrophenylazo)-5,5'-di-tert-butyl-1,1'-biphenyl-2,2'-diol

Product 1

HCID 1356276063,3'-bis-(2H-benzotriazol-2-yl)-5,5'-di-tert-butyl-1,1'-biphenyl-2,2'-diolYield 25.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A mixture of the 3,3′-bis-(2-nitrophenylazo)-5,5′-di-tert-butyl-1,1′-biphenyl-2,2′-diol (3.5 g), zinc powder (6.38 g), 15% aqueous sodium hydroxide (20 ml), and ethanol (40 ml) was boiled under reflux in a nitrogen atmosphere for three hours. The hot mixture was filtered over diatomaceous earth. After cooling in an ice bath and acidification with hydrochloric acid, the precipitated product was collected by suction filtration, washed with water and air dried. Purification of the crude product by dry column chromatography using a mixture of hexane and ethyl acetate (9:1 v/v) as the eluent gave pure 3,3′-bis-(2H-benzotriazol-2-yl)-5,5′-di-tert-butyl-1,1′-biphenyl-2,2′-diol (COMPOUND 2) (0.8 g); m.p. 234° C.

Workup

  1. temperatureunder reflux in a nitrogen atmosphere for three hours
  2. filtrationThe hot mixture was filtered over diatomaceous earth
  3. temperatureAfter cooling in an ice bath
  4. filtrationacidification with hydrochloric acid, the precipitated product was collected by suction filtration
  5. washwashed with water and air
  6. customdried
  7. customPurification of the crude product
  8. customby dry column chromatography
  9. additiona mixture of hexane and ethyl acetate (9:1 v/v) as the eluent

Sources & evidence

ORD record
ord-94bb5ab4647f4a62a3851ef65c300f14
Source dataset
uspto-grants-2002_02
Patent number
US06344505B1

Reaction notes

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