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

HRID 1763176Notes

Reaction equation

HRID 1763176 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

97% sodium hydroxide 14.4 g was added to a mixture of methanol 72 ml and water 36 ml. 2-nitro-2'-hydroxy-5'-t-butylazobenzene 15.0 g was then added to the resultant mixture and the mixture was heated to 45°~50° C. Hydroquinone 0.4 g and then glucose 5.0 g were added to the heated mixture over 30 minutes while stirring. The mixture was further stirred for one hour. As this result, the azobenzene disappeared to produce 2-(2'-hydroxy-5'-t-butylphenyl)benzotriazole-N-oxide, thus the reaction of Process (b) being completed.

Workup

  1. temperaturethe mixture was heated to 45°~50° C
  2. stirringThe mixture was further stirred for one hour

Sources & evidence

ORD record
ord-4348971d521a484f8651052e05ba1d5f
Source dataset
uspto-grants-1989_05
Patent number
US04835284

Reaction notes

Loading…