Hydrochloric Acid → 1-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one

HRID 483768

反応式

HRID 483768 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].Cl.[C:11](OC(=O)C)(=[O:13])[CH3:12]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([C:11](=[O:13])[CH3:12])[CH:5]=[C:4]([Br:8])[C:3]=1[OH:9]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 118472,6-Dibromophenol

生成物 1

HCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

In 5 ml of acetic anhydride was dissolved 5.0 g of 2,6-dibromophenol and, one drop of conc. sulfuric acid was added to the solution. While sometimes manually shaking, the mixture was stirred. When generation of heat stopped, the solution was poured onto 50 ml of ice water and the precipitated crystals of acetic acid-2,6-dibromophenyl were taken by filtration. The crystals were washed with chilled water and dried under reduced pressure. Next, this acetic acid-2,6-dibromophenyl was dissolved in 20 ml of nitrobenzene and 4.0 g of powdery aluminum chloride was gradually added to the solution. The reaction was carried out at 60° to 70° C. for 50 hours to effect Fries rearrangement. After completion of the reaction, the reaction solution was poured onto 100 ml of cold dil. hydrochloric acid. After allowing to stand at 5° C. overnight, the precipitated crystals were taken out by filtration, washed with n-hexane and dried under reduced pressure to give 3.87 g of 2,6-dibromo-4-acetylphenol as crude crystals. The crystals were recrystallized from hot ethyl acetate to give 2.42 g of pure 2,6-dibromo-4-acetylphenol as light brown crystals. 2,6-Dibromo-4-acetylphenol (3,5-dibromo-4-hydroxyacetophenone): C8H6Br2O2

後処理

  1. additionwas added to the solution
  2. stirringthe mixture was stirred
  3. temperatureWhen generation of heat
  4. filtrationthe precipitated crystals of acetic acid-2,6-dibromophenyl were taken by filtration
  5. washThe crystals were washed with chilled water
  6. customdried under reduced pressure
  7. dissolutionNext, this acetic acid-2,6-dibromophenyl was dissolved in 20 ml of nitrobenzene
  8. addition4.0 g of powdery aluminum chloride was gradually added to the solution
  9. customAfter completion of the reaction
  10. waitto stand at 5° C. overnight
  11. filtrationthe precipitated crystals were taken out by filtration
  12. washwashed with n-hexane
  13. customdried under reduced pressure

出典と根拠

ORDレコード
ord-681c486a916a4b25b01bcfca59fab776
出典データセット
uspto-grants-1993_07
特許番号
US05227291

関連ノート

読み込み中…