2-Nitrophenol → 1-(Cyclopentyloxy)-2-nitrobenzene

HRID 262012ノート

反応式

HRID 262012 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH:11]1(Br)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:11]1([O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

5

反応物 3

HCID 69472-NitrophenolHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

生成物 1

HCID 221644731-(Cyclopentyloxy)-2-nitrobenzene収率 46.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

2-Nitrophenol (83.5 g, 0.60 mole), cyclopentyl bromide (98.0 g, 0.66 mole), anhydrous potassium carbonate (82.9 g, 0.60 mole) and dry acetone (600 cc) were refluxed for 72 hrs., and filtered to remove the potassium bromide. The residue was washed with acetone and the solvent was removed by rotary evaporation. The residue was partitioned between 200 cc of dichloromethane and water. The dichloromethane layer was washed with 200 cc of 10% potassium hydroxide, separated and the solvent was removed by rotary evaporation. The crude product was fractionally distilled at 144°-146° C. at 1.0 mm. Hg to yield 58.2 g of product (46.8%).

後処理

  1. filtration, and filtered
  2. customto remove the potassium bromide
  3. washThe residue was washed with acetone
  4. customthe solvent was removed by rotary evaporation
  5. customThe residue was partitioned between 200 cc of dichloromethane and water
  6. washThe dichloromethane layer was washed with 200 cc of 10% potassium hydroxide
  7. customseparated
  8. customthe solvent was removed by rotary evaporation
  9. distillationThe crude product was fractionally distilled at 144°-146° C. at 1.0 mm. Hg

出典と根拠

ORDレコード
ord-9cc3f965c1b640e1b7d43fc85411ead5
出典データセット
uspto-grants-1979_05
特許番号
US04153446

反応ノート

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