4-Hydroxybenzyl Alcohol → {4-[(3,4-Dinitrophenyl)oxy]phenyl}methanol

HRID 547609

反応式

HRID 547609 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N+:11]([C:4]1[CH:3]=[C:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][OH:14])=[CH:17][CH:18]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])([O-:13])=[O:12]

参加物

6

反応物 4

HCID 1254-Hydroxybenzyl AlcoholHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 2986753,4-Dinitrofluorobenzene

生成物 1

HCID 57585910{4-[(3,4-Dinitrophenyl)oxy]phenyl}methanol収率 45.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-fluoro-1,2-dinitrobenzene (20.0 g, 107.5 mmol), 4-(hydroxymethyl)phenol (14.7 g, 118.2 mmol) and potassium carbonate (17.8 g, 129.0 mmol) were stirred in 250 ml of dimethylformamide at room temperature for approximately 17 hours. The reaction was heated at 35 degree Centigrade for 1.5 hours. Cesium carbonate (2 g, 6.14 mmol) was added and the reaction was heated at 45 deg. C. for approximately 22 hours. The solids were filtered away and washed with ethyl acetate. The filtrate was diluted with water and extracted 4 times with ethyl acetate. The ethyl acetate layers were washed with a water/brine mixture 5 times. The aqueous wash layers were back extracted with ethyl acetate twice. The organic layers were combined, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0 to 100% ethyl acetate in hexane) to give 14.1 g of {4-[(3,4-dinitrophenyl)oxy]phenyl}methanol.

後処理

  1. temperatureThe reaction was heated at 35 degree Centigrade for 1.5 hours
  2. temperaturethe reaction was heated at 45 deg. C
  3. filtrationThe solids were filtered away
  4. washwashed with ethyl acetate
  5. additionThe filtrate was diluted with water
  6. extractionextracted 4 times with ethyl acetate
  7. washThe ethyl acetate layers were washed with a water/brine mixture 5 times
  8. extractionThe aqueous wash layers were back extracted with ethyl acetate twice
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (0 to 100% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-1e841c2472d34406894f9a6e49077704
出典データセット
uspto-grants-2011_05
特許番号
US07939528B2

関連ノート

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