Hydrogen Peroxide → 1,3-Dichloro-2-nitrobenzene

HRID 1470700

反応式

HRID 1470700 の反応式
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:8]=1[NH2:9].OO.[OH-:17].[Na+]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCC.ClC1C=CC=CC=1.O[W](O)(=O)=O>[Cl:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:8]=1[N+:9]([O-:2])=[O:17]

参加物

8

反応物 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 118462,6-Dichloroaniline2 回HCID 14798Sodium Hydroxide

生成物 1

HCID 117591,3-Dichloro-2-nitrobenzene収率 63%

試薬・触媒・溶媒 3

HCID 1152Tungstic acid触媒HCID 14250Tetradecyltrimethylammonium bromide触媒HCID 7964Chlorobenzene溶媒2 回

反応条件

温度
47 °C

実験手順

A solution of 7.5 g (30 mmol) of tungstic acid, 5.2 g (52 mmol) of concentrated sulfuric acid, 32.7 g (200 mmol) of 2,6-dichloroaniline, and 5.84 g (20 mmol) of myristyltrimethylammonium bromide in 74 ml of a chlorobenzene was heated to 47° C., and 53 ml (600 mmol) of a 35% hydrogen peroxide solution was added dropwise over 10 hours. The pH value at this time was 0.3. After the completion of the dropwise addition, the mixture was stirred at 47° C. for 4 hours. After the disappearance of the 2,6-dichloroaniline was confirmed by HPLC analysis (area percentage method), 220 ml of chlorobenzene and 20 g (160 mmol) of a 25% aqueous sodium hydroxide solution were added. The pH value at this time was 13.5. The reaction liquid was separated at 75° C., and 91 g of the aqueous layer was removed. Then, the obtained organic layer was cooled to 60° C. or less. 35 g (300 mmol) of a 48% aqueous potassium hydroxide solution was added, and 34 ml (400 mmol) of a 35% hydrogen peroxide solution was added dropwise while the reaction temperature was adjusted to 60° C. or less. After the completion of the dropwise addition, the mixture was stirred at 60° C. for 2 hours, and the reaction was completed. The reaction liquid was separated at room temperature. The obtained organic layer was analyzed by gas chromatography by the absolute calibration method, and as a result, the yield was 63%.

後処理

  1. additionAfter the completion of the dropwise addition
  2. additionwere added
  3. customThe reaction liquid
  4. customwas separated at 75° C.
  5. custom91 g of the aqueous layer was removed
  6. temperatureThen, the obtained organic layer was cooled to 60° C. or less
  7. addition35 g (300 mmol) of a 48% aqueous potassium hydroxide solution was added
  8. addition34 ml (400 mmol) of a 35% hydrogen peroxide solution was added dropwise while the reaction temperature
  9. customwas adjusted to 60° C. or less
  10. additionAfter the completion of the dropwise addition
  11. stirringthe mixture was stirred at 60° C. for 2 hours
  12. customThe reaction liquid
  13. customwas separated at room temperature

出典と根拠

ORDレコード
ord-a2d2235c8f664a8099e00ead4b53f3cc
出典データセット
uspto-grants-2015_04
特許番号
US09006477B2

関連ノート

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