Hydroquinone → 2-(2-hydroxy-5-t-butylphenyl)benzotriazole-N-oxide

HRID 257657

Reaction equation

HRID 257657 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]=[N:13][C:14]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[CH:16][C:15]=1[OH:24])([O-])=[O:4].C1(C=CC(O)=CC=1)O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.N(C1C=CC=CC=1)=NC1C=CC=CC=1>O.CO>[OH:24][C:15]1[CH:16]=[CH:17][C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:19][C:14]=1[N:13]1[N+:3]([O-:4])=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=[N:12]1

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 2272AzobenzeneHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 1355145822-Nitro-2'-hydroxy-5'-t-butylazobenzene

Product 1

HCID 139071722-(2-hydroxy-5-t-butylphenyl)benzotriazole-N-oxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Example 7 of U.S. Pat. No. 4,835,284 is duplicated. 97% sodium hydroxide (14.4 g) is added to a mixture of methanol (72 ml) and water (36 ml). 2-nitro-2'-hydroxy-5'-t-butylazobenzene (15.0 g) is then added to the resultant mixture and the mixture is heated to 45°-5020 C. Hydroquinone (0.4 g) and then glucose (5.0 g) are added to the heated mixture over 30 minutes while stirring. The mixture is further stirred for one hour. As this result, the azobenzene disappears to produce 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole-N-oxide. 9-fluorenone (0.7 g) is then added to the reaction liquor thus obtained, and the liquor is heated to 55°-60° C. Thereafter, glucose (6.0 g) is added to the reaction liquor over 30 minutes, and the reaction is conducted at 75° C. (boiling point) for 6 hours. As a result, the N-oxide disappears. Thereafter, the pH of the reaction liquor is brought to 8 with 62% sulfuric acid (19.0 g) to precipitate a crystal. The precipitated crystal is separated by filtration, and the separated crystal is fully washed with water and further with methanol. The washed crystal is then dried, thus obtaining 11.6 g of 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole. One can see that the reaction using an aromatic ketone takes over 8 hours to complete. Two catalysts are also required.

Workup

  1. temperaturethe mixture is heated to 45°-5020 C
  2. stirringThe mixture is further stirred for one hour

Sources & evidence

ORD record
ord-f2879cef9a084e15869b438b68906f31
Source dataset
uspto-grants-1993_11
Patent number
US05262541

Linked notes

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