1,2-Dichlorobenzene → 2-(6-Hydroxy-2-naphthyl)-5-butylbenzooxazole

HRID 5283

反応式

HRID 5283 の反応式
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([NH:17][C:18]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][CH3:27])[CH:21]=[CH:20][C:19]=1[OH:28])=O)[CH:9]=[CH:8]2)(=O)C.C1C=C(Cl)C(Cl)=CC=1.Cl(O)(=O)=O>O>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]1[O:28][C:19]3[CH:20]=[CH:21][C:22]([CH2:24][CH2:25][CH2:26][CH3:27])=[CH:23][C:18]=3[N:17]=1)[CH:9]=[CH:8]2

参加物

5

反応物 3

HCID 72391,2-Dichlorobenzene2 回HCID 19654Chloric acidHCID 197954112-(6-Acetoxy-2-naphthoylamino)-4-butylphenol

生成物 1

HCID 1357271132-(6-Hydroxy-2-naphthyl)-5-butylbenzooxazole収率 48%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
201.5 °C

実験手順

5.40 g (14.3 m mole) of 2-(6-acetoxy-2-naphthoylamino)-4-butylphenol, 0.43 g of p-toluenesulfuric acid monohydrate and 40 ml of O-dichlorobenzene were placed in a 100 ml round-bottom flask, followed by heating and stirring for 30 minutes at 200-203° C. After the reaction, O-dichlorobenzene was distilled off under reduced pressure. To the resultant, 2.00 g (30.3 m mole) of potassium hydroxide and 60 ml of ethanol were added, followed by heating and stirring for 20 minutes at 60° C. After the reaction, the reaction mixture was poured into 600 ml of water. To the reaction mixture, 8 ml of chloric acid was added to precipitate a crystal. The crystal was filtered, washed with water and recrystallized from a mixture solvent of acetoneethanol to obtain 2.18 g of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole (Yield: 42.4%).

後処理

  1. temperatureby heating
  2. distillationwas distilled off under reduced pressure
  3. additionTo the resultant, 2.00 g (30.3 m mole) of potassium hydroxide and 60 ml of ethanol were added
  4. temperatureby heating
  5. stirringstirring for 20 minutes at 60° C
  6. customAfter the reaction
  7. customto precipitate a crystal
  8. filtrationThe crystal was filtered
  9. washwashed with water
  10. customrecrystallized from a mixture solvent of acetoneethanol

出典と根拠

ORDレコード
ord-f954faeda5054c7c942ac3ce9dae5608
出典データセット
uspto-grants-1993_09
特許番号
US05244596

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