Sodium Hydroxide → 5-Phenyl-2-(2-hydroxy-3-phenyl-5-tert-octylphenyl)-2H-benzotriazole

HRID 859067Notes

Reaction equation

HRID 859067 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])=[CH:6][C:5]=1[N:24]=[N:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][C:27]=1[N+:38]([O-])=O>O>[C:32]1([C:29]2[CH:30]=[CH:31][C:26]3=[N:25][N:24]([C:5]4[CH:6]=[C:7]([C:16]([CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:17])[CH:8]=[C:9]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[C:4]=4[OH:3])[N:38]=[C:27]3[CH:28]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1363776762-Hydroxy-2'nitro3,4'-diphenyl-5-tert-octylazobenzene2×

Product 1

HCID 235012165-Phenyl-2-(2-hydroxy-3-phenyl-5-tert-octylphenyl)-2H-benzotriazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of sodium hydroxide (6 g, 0.15 mol) in 8 mL of water is added 2-hydroxy-2′nitro-3,4′-diphenyl-5-tert-octylazobenzene (6.56 g), prepared in (D) above. The reaction mixture is heated to reflux and then formadine sulfinic acid (10.8 g, 0.1 mol) is added portionwise over 20 minutes. The reaction mixture is heated at reflux for 1.5 hours. To the cooled reaction mixture is added 200 mL of water and the ethanol is removed under vacuum. The reaction mixture is adjusted to pH 4 with hydrochloric acid. The resultant mixture is extracted twice with methylene chloride and the combined organic phases are extracted with water. The organic phase is dried ovdr anhydrous magnesium sulfate, and the solvent is then removed under vacuum. The residue is recrystallized sequentially from a mixture of water and methanol, and petroleum ether to give the title compound as a white solid melting at 123–125° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for 1.5 hours
  5. customTo the cooled reaction mixture
  6. customthe ethanol is removed under vacuum
  7. extractionThe resultant mixture is extracted twice with methylene chloride
  8. extractionthe combined organic phases are extracted with water
  9. dry with materialThe organic phase is dried ovdr anhydrous magnesium sulfate
  10. customthe solvent is then removed under vacuum
  11. customThe residue is recrystallized sequentially from a mixture of water and methanol, and petroleum ether

Sources & evidence

ORD record
ord-615b3e757733439097e0243b64190d9e
Source dataset
uspto-grants-2006_12
Patent number
US07148274B2

Reaction notes

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