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

HRID 339004

반응식

HRID 339004 반응식
[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]

참가 물질

7

반응물 3

HCID 6497Dimethyl SulfateHCID 119232-Nitrobenzyl alcoholHCID 14798Sodium Hydroxide

생성물 1

HCID 126166891-(Methoxymethyl)-2-nitrobenzene수율 91.4%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ce3c4966cc3415d84870434888c0353
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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