Sulfuric Acid → 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide

HRID 2166257

Reaktionsgleichung

Reaktionsgleichung von HRID 2166257
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[N:11]=[N:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=1[OH:24])([O-])=O.[OH-].[Na+].C1C2C(=[O:40])C3C(=CC=CC=3)C=2C=CC=1.N(C1C=CC=CC=1)=NC1C=CC=CC=1.S(=O)(=O)(O)O>O.C(O)CCC>[OH:24][C:14]1[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[N:12]1[N+:11]([O-:40])=[C:5]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]2=[N:1]1

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 2272AzobenzeneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 89771Phenol, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-6-(1,1-dimethylethyl)-4-methyl-

Produkt 1

HCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxideAusbeute 745,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-nitro-4-chloro-2'-hydroxy-3'-t-butyl-5'-methylazobenzene 23.2 g was added to a mixture of n-butanol 60 g, water 10.6 g and 97% sodium hydroxide 6.9 g, and the resultant mixture was stirred while raising temperature to 65° C. Thereafter, the mixture was cooled to 50° C., and 9-fluorenone 1.5 g was added to the mixture. The reaction mixture was then heated to 90° C. in one hour, and the mixture was stirred at 90°~96° C. for five hours to effect reaction, thus almost all of the azobenzene having disappeared. Thereafter, water 50 ml was added to the reaction liquor, and the reaction liquor was neutralized to pH 8~9 with 62% sulfuric acid 10 g to precipitate a crystal. The crystal thus obtained was filtered to separate the crystal, and the separated crystal was then fully washed with water and further with a small amount of methanol. The washed crystal was then dried, thus producing 20.6 g of 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide having a melting point of 160° to 163° C. at the yield of 93.0%.

Aufarbeitung

  1. temperatureThereafter, the mixture was cooled to 50° C.
  2. temperatureThe reaction mixture was then heated to 90° C. in one hour
  3. customreaction
  4. customto precipitate a crystal
  5. customThe crystal thus obtained
  6. filtrationwas filtered
  7. customto separate the crystal
  8. washthe separated crystal was then fully washed with water and further with a small amount of methanol
  9. customThe washed crystal was then dried

Quellen und Nachweise

ORD-Eintrag
ord-eae97202b9914dd7b1d4b40082fa7b76
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04943637

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