Water → 2-Methoxy-4-nitrobenzenethiol

HRID 856695ノート

反応式

HRID 856695 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1O.C(N(CC)CC)C.FC(F)(F)[S:22](OS(C(F)(F)F)(=O)=O)(=O)=O.O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[SH:22]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 767382-Methoxy-4-nitrophenol

生成物 1

HCID 221487412-Methoxy-4-nitrobenzenethiol収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-methoxy-4-nitrophenol (19.2 g) was dissolved in methylene chloride (192 ml), triethylamine (20.5 ml) was added to the mixture, trifluoromethanesulfonic acid anhydride (23.0 ml) was added dropwise to the solution at 0° C., and the mixture was stirred for 1 hour at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, the obtained residue was dissolved in ethanol (274 ml) under heat reflux, and an aqueous solution (342 ml) of sodium sulfate nanohydrate (21.1 g) and sulfur (2.8 g) in ethanol was added dropwise thereto for 20 minutes. Aqueous solution of sodium hydroxide (7.02 g, 28.1 ml) was added dropwise to the solution for 20 minutes, and then, the mixture was cooled to room temperature, ice-water was added thereto. The precipitates were filtered, and the pH of the filtrate was adjusted to about pH 5 with 6N hydrochloric acid, and the precipitates were collected by filtration, and washed with water to give 2-methoxy-4-nitrobenzenethiol (15.8 g, 75%).

後処理

  1. additionwas added dropwise to the solution at 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe obtained residue was dissolved in ethanol (274 ml)
  7. temperatureunder heat
  8. temperaturereflux
  9. additionan aqueous solution (342 ml) of sodium sulfate nanohydrate (21.1 g) and sulfur (2.8 g) in ethanol was added dropwise
  10. waitfor 20 minutes
  11. additionAqueous solution of sodium hydroxide (7.02 g, 28.1 ml) was added dropwise to the solution for 20 minutes
  12. temperaturethe mixture was cooled to room temperature
  13. additionice-water was added
  14. filtrationThe precipitates were filtered
  15. filtrationthe precipitates were collected by filtration
  16. washwashed with water

出典と根拠

ORDレコード
ord-9ec5bb4b1db149dca88223c64673a967
出典データセット
uspto-grants-2007_08
特許番号
US07262185B2

反応ノート

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