1-Butanol → UV-328

HRID 2166266Notes

Reaction equation

HRID 2166266 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N+:22]([O-])=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1.C(O)CCC.[OH-].[Na+].C1C2C(=O)C3C(=CC=CC=3)C=2C=CC=1>O>[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N:22]=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 111431102-(2H-Benzotriazol-2-yl)-4,6-bis(tert-pentyl)phenol N-oxide

Product 1

HCID 33263UV-328Yield 92.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(2-hydroxy-3,5-di-t-amylphenyl)benzotriazole-N-oxide 23.2 g was added to a mixture of n-butanol 60 g, water 12 g and 97% sodium hydroxide 16.5 g, and 9-fluorenone 2.0 g was further added to the resultant mixture. The resultant mixture was heated to 80° C., and was further stirred at 80°~85° C. for 2.5 hours, thus the reduction reaction being completed. The reaction liquor was treated in the same manner as in Example 17 to recover butanol, and 1.8 g of 9-fluorenone catalyst was recovered as a fraction at 120°~130° C. under vacuum of 2~3 mmHg. After recovering the catalyst, the remaining material was washed with methanol to produce the desired product, i.e. 20.5 g of 2-(2-hydroxy-3,5-di-t-amylphenyl)benzotriazole having a melting point of 79°~80° C. at the yield of 92.8%.

Workup

  1. customthus the reduction reaction
  2. additionThe reaction liquor was treated in the same manner as in Example 17
  3. customto recover butanol, and 1.8 g of 9-fluorenone catalyst
  4. customwas recovered as a fraction at 120°~130° C. under vacuum of 2~3 mmHg
  5. customAfter recovering the catalyst
  6. washthe remaining material was washed with methanol

Sources & evidence

ORD record
ord-57972ed3ec024a77926e8f7e74e76af0
Source dataset
uspto-grants-1990_07
Patent number
US04943637

Reaction notes

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