Nitric Acid → 4-Nitro-3,5-bis(trifluoromethyl)phenol

HRID 1373732ノート

反応式

HRID 1373732 の反応式
[N+:1]([O-:4])([OH:3])=[O:2].[F:5][C:6]([F:19])([F:18])[C:7]1[CH:8]=[C:9]([OH:17])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1>C(O)(=O)C>[N+:1]([C:8]1[C:7]([C:6]([F:5])([F:18])[F:19])=[CH:12][C:11]([C:13]([F:14])([F:15])[F:16])=[CH:10][C:9]=1[OH:17])([O-:4])=[O:2].[N+:1]([C:12]1[C:7]([C:6]([F:18])([F:19])[F:5])=[CH:8][C:9]([OH:17])=[CH:10][C:11]=1[C:13]([F:15])([F:14])[F:16])([O-:3])=[O:2]

参加物

5

反応物 2

HCID 944Nitric AcidHCID 676803,5-Bis(trifluoromethyl)phenol

生成物 2

HCID 210755992-Nitro-3,5-bis(trifluoromethyl)phenolHCID 210756024-Nitro-3,5-bis(trifluoromethyl)phenol収率 59.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Fuming nitric acid (8.22 mL, 198.2 mmol) was added dropwise to a solution of 3,5-bis(trifluoromethyl)phenol (28.5 g, 123.9 mmol) in acetic acid (300 mL) at about 10° C. After being elevated to room temperature, the mixture was stirred for 43 hours. The reaction mixture was poured into ice water and the resulting solution was extracted with ethyl acetate. The organic layers were combined, washed successively with water and saturated saline, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=15:1→10:1) to yield a crude product. The crude product thus obtained was subjected to sublimation separation under reduced pressure (3 mmHg) at 80° C. by using an evaporator to distill off the isomer, that is, 2-nitro-3,5-bis(trifluoromethyl)phenol, whereby 10.1 g (yield: 29.7%) of 4-nitro-3,5-bis(trifluoromethyl)phenol was obtained as yellow needle-like crystals.

後処理

  1. customAfter being elevated to room temperature
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed successively with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=15:1→10:1)
  8. customto yield a crude product
  9. customThe crude product thus obtained
  10. customwas subjected to sublimation separation under reduced pressure (3 mmHg) at 80° C.
  11. customan evaporator
  12. distillationto distill off the isomer

出典と根拠

ORDレコード
ord-ab342dc5df01417488f4ca28541588f7
出典データセット
uspto-grants-2007_01
特許番号
US07163944B2

反応ノート

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