Dimethyl Sulfate → 1-(Methoxymethyl)-2-nitrobenzene

HRID 339004

反応式

HRID 339004 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][OH:11])([O-:3])=[O:2].[OH-].[Na+].[CH3:14]OS(OC)(=O)=O>C(Cl)Cl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:14][O:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

参加物

7

反応物 3

HCID 6497Dimethyl SulfateHCID 119232-Nitrobenzyl alcoholHCID 14798Sodium Hydroxide

生成物 1

HCID 126166891-(Methoxymethyl)-2-nitrobenzene収率 91.4%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (2-nitrophenyl)methanol (5.13 g, 33.50 mmol) in DCM (75 mL) was added 3.35 N NaOH (75 mL, 251.2 mmol) in water at ambient temperature and stirred at ambient temperature for 10 minutes. Me2SO4 (6.38 ml, 67.0 mmol) and tetrabutylammonium hydrogen sulfate (0.57 g, 1.68 mmol) were added and the mixture stirred vigorously for 20 hours at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 1-(methoxymethyl)-2-nitrobenzene (5.12 g, 91.4%) as an oil.

後処理

  1. stirringthe mixture stirred vigorously for 20 hours at ambient temperature
  2. customwas separated
  3. washwashed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-3ce3c4966cc3415d84870434888c0353
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

読み込み中…