Acetic Acid → 1,2-Phenanthrenedione

HRID 382922

反応式

HRID 382922 の反応式
[CH:1]1[C:14]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=CC=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:15]([OH:18])(=O)[CH3:16].Br([O-])(=O)=[O:20].[K+].BrBr>O>[C:15]1(=[O:18])[C:16]2[CH:8]=[CH:7][C:6]3[C:5](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=[CH:2][C:1]1=[O:20]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 995PhenanthreneHCID 24408BromineHCID 23673461Potassium Bromate

生成物 1

HCID 30805661,2-Phenanthrenedione収率 80%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
72.5 °C

実験手順

Phenanthrene (16 g, Aldrich Tech Grade (90 percent), 0.081 mol) and acetic acid (200 ml) were stirred and heated to 70-75° C. Potassium bromate (32 g, 0.19 mol) was added in 2 portions. After the addition of the first portion the temperature rose to reflux with evolution of bromine vapors. The second portion was added and the condenser was replaced by a distillation head. The heating was continued until the distillate was colorless. The deep red solution was cooled and poured into water (300 ml) and the precipitate was isolated by filtration. The crude product was purified by reslurrying in 100 ml of hot (70° C.) aqueous sodium bisulfite solution (40 percent) and filtering while hot. The deep red filtrate was cooled and treated with aqueous sodium carbonate until basic. The precipitated product was recovered by extraction with methylene chloride, dried and concentrated to yield 13.4 g (80 percent yield) of orange yellow solid: mp 182-184° C.

後処理

  1. additionAfter the addition of the first portion the temperature
  2. additionThe second portion was added
  3. temperatureThe deep red solution was cooled
  4. customthe precipitate was isolated by filtration
  5. customThe crude product was purified
  6. customby reslurrying in 100 ml of hot (70° C.) aqueous sodium bisulfite solution (40 percent)
  7. filtrationfiltering while hot
  8. temperatureThe deep red filtrate was cooled
  9. additiontreated with aqueous sodium carbonate until basic
  10. customThe precipitated product was recovered by extraction with methylene chloride
  11. customdried
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-f340790ec03b4833bd68969d8dffd5ca
出典データセット
uspto-grants-2001_10
特許番号
US06310256B1

関連ノート

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