Hydroquinone → 2-(2-hydroxy-5-methylphenyl)benztriazole N-oxide

HRID 1763182Notes

Reaction equation

HRID 1763182 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]([CH3:18])[CH:15]=[CH:14][C:13]=1[OH:19])([O-])=[O:2].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.[N+](C1C=CC=CC=1N=NC1C=C(C(CC)(C)C)C=C(C(CC)(C)C)C=1O)([O-])=O.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[OH:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[N:11]1[N+:1]([O-:2])=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:10]1

Participants

9

Reactant 6

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 2272AzobenzeneHCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenolHCID 1041112-Nitro-2'-hydroxy-3',5'-bis(tert-amyl)azobenzeneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Water 70 ml, 97% sodium hydroxide, 5.2 g, 2-nitro-2'-hydroxy-5'-methylazobenzene 12.9 g and toluene 10 ml were mixed and heated to 60° C. After stirring, hydroquinone 0.6 g was added and glucose 5.0 g was added to the mixture over one hour at 40° to 45° C. The mixture was further stirred for two hours, and the azobenzene disappeared, thus the reaction of Process (b) being completed. The reaction liquor was neutralized with 62% sulfuric acid 5.8 g, and was cooled to 20° C. to precipitate a crystal. The crystal thus precipitated was separated by filtration and was dried, thus producing 10.8 g of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole-N-oxide having a melting point of 138° to 140° C. at the yield of 90.0%.

Workup

  1. stirringThe mixture was further stirred for two hours
  2. temperaturewas cooled to 20° C.
  3. customto precipitate a crystal
  4. customThe crystal thus precipitated
  5. customwas separated by filtration
  6. customwas dried

Sources & evidence

ORD record
ord-a8628672157348ffbc214da3deea841c
Source dataset
uspto-grants-1989_05
Patent number
US04835284

Reaction notes

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