Benzoic Acid → 6-Bromo-2-(4-nitrophenyl)-1,3-benzodioxan

HRID 248805

反応式

HRID 248805 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH2:7][OH:8].[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12].C(O)(=O)C1C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:18]([C:17]3[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=3)[O:8][CH2:7][C:6]=2[CH:9]=1

参加物

5

反応物 3

HCID 243Benzoic AcidHCID 5414-NitrobenzaldehydeHCID 753425-Bromo-2-hydroxybenzyl alcohol

生成物 1

HCID 189611956-Bromo-2-(4-nitrophenyl)-1,3-benzodioxan収率 70%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

An intimately ground mixture of 5-bromo-2hydroxybenzyl alcohol (4.06 g), 4-nitrobenzaldehyde (3.93 g) and benzoic acid (0.2 g) was stirred and heated to 85° C. (±5° C.) under nitrogen for 88 hours. The clear melt which formed initially gradually solidified throughout the reaction period. The resulting solidified mass was cooled and dissolved in ethyl acetate (250 ml). The solution was then washed with 20% aqueous sodium carbonate, 20% aqueous sodium bisulphite and finally with brine. After drying over sodium sulphate, the organic phase was evaporated to yield a solid residue which was purified by briefly suspending in hot ethanol (approx. 75 ml) and cooling to 0°-5° C. The pure product was obtained as pale buff-coloured crystals (4.69g, 70%), mp 163°-164° C.

後処理

  1. customThe clear melt which formed initially gradually
  2. customsolidified throughout the reaction period
  3. temperatureThe resulting solidified mass was cooled
  4. washThe solution was then washed with 20% aqueous sodium carbonate, 20% aqueous sodium bisulphite and finally with brine
  5. dry with materialAfter drying over sodium sulphate
  6. customthe organic phase was evaporated
  7. customto yield a solid residue which
  8. customwas purified
  9. temperaturecooling to 0°-5° C

出典と根拠

ORDレコード
ord-246961ac753c41a7b1297a7ca94aeffc
出典データセット
uspto-grants-1993_05
特許番号
US05212171

関連ノート

読み込み中…