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

HRID 2166262

反応式

HRID 2166262 の反応式
[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.C1C(O)=CC(O)=C(C(C2C=CC(O)=CC=2O)=O)C=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

参加物

9

反応物 6

HCID 1118Sulfuric AcidHCID 2272AzobenzeneHCID 85712,2',4,4'-TetrahydroxybenzophenoneHCID 10241FluorenoneHCID 14798Sodium HydroxideHCID 89771Phenol, 2-[2-(4-chloro-2-nitrophenyl)diazenyl]-6-(1,1-dimethylethyl)-4-methyl-

生成物 1

HCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide収率 829.1%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒2 回

反応条件

温度
65 °C

実験手順

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 to finish the reaction of Process (b). Thereafter, water 50 ml was added to the reaction mixture, and the mixture was neutralized to pH 8~9 with 62% sulfuric acid 10 g. The neutralized liquor was cooled to 20° C. to precipitate a crystal. The crystal thus precipitated was separated by filtration, thus producing the wet product 22.9 g of 2-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxide (dry product: 20.6 g, yield: 93.0%, melting point: 160°~163° C.).

後処理

  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. temperatureThe neutralized liquor was cooled to 20° C.
  5. customto precipitate a crystal
  6. customThe crystal thus precipitated
  7. customwas separated by filtration

出典と根拠

ORDレコード
ord-0480d5fda07e400db85359389b6c23c5
出典データセット
uspto-grants-1990_07
特許番号
US04943637

関連ノート

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