Dimethyl Sulfate → 2-Methoxy-6-(1-methylethyl)naphthalene

HRID 1975525노트

반응식

HRID 1975525 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:8]=2)[CH:3]=1.[OH-].[Na+].[CH3:17]OS(OC)(=O)=O>O>[CH3:17][O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:12]([CH3:14])[CH3:13])[CH:8]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl Sulfate2회HCID 14798Sodium Hydroxide3회HCID 104650462-Naphthalenol, 6-(1-methylethyl)-

생성물 1

HCID 1245012-Methoxy-6-(1-methylethyl)naphthalene

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a suspension of 31.71 g 2-hydroxy-6-(1-methylethyl)naphthalene in 500 ml water and under a nitrogen atmosphere was added 61.5 g of 14.4% (by weight) sodium hydroxide (NaOH). The mixture was heated to 60° C. and 30.02 g of dimethylsulfate was added in one portion to the dark cloudy solution. In 20 minutes the pH of the reaction had dropped from 13 to 2. Another 20 g 14.4% NaOH was added. After 45 minutes 10 g additional dimethylsulfate was added. After 1 hour 20 g of 14.4% NaOH was added and the reaction was heated at 80° C. overnight. The brown suspension was then extracted with toluene and the extract was dried over magnesium sulfate (MgSO4), filtered, and concentrated in vacuum to give a crude solid which was recrystallized from isopropanol to give 2-methoxy-6-isopropylnaphthalene, melting point 63.5° to 64.5° C.

후처리

  1. additionIn 20 minutes the pH of the reaction had dropped from 13 to 2
  2. temperaturethe reaction was heated at 80° C. overnight
  3. extractionThe brown suspension was then extracted with toluene
  4. dry with materialthe extract was dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customto give a crude solid which
  8. customwas recrystallized from isopropanol

출처 및 근거

ORD 기록
ord-dea392d0f63244949da540bfeef8e20a
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05286902

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