Water → 1,5-Dimethoxynaphthalene

HRID 575493

반응식

HRID 575493 반응식
[C:1]1(O)[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].S(OC)(O[CH3:23])(=O)=O.O>CC(C)=O>[CH3:23][O:11][C:6]1[C:5]2[C:10](=[C:1]([O:16][CH3:13])[CH:2]=[CH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 67491,5-DihydroxynaphthaleneHCID 11430Potassium Carbonate

생성물 1

HCID 2525271,5-Dimethoxynaphthalene수율 95.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Naphthalene-1,5-diol (16.0 g, 100 mmol) and potassium carbonate (27.6 g, 200 mmol) were stirred in acetone (300 mL) and dimethyl sulfate (32 mL) was added using syringe. The mixture was then heated to reflux under nitrogen overnight. Water (300 mL) was added after the mixture was cooled to room temperature. The precipitate was collected by filtration and washed with water (4×50 mL), then methanol (3×50 mL). After drying under vacuum, the solid was heated at reflux in ethanol (300 mL) for 2 hours. After cooling to room temperature, the desired product was then collected by filtration to give a pale brown solid (17.9 g, 95.2%). 1H NMR (500 MHz, CDCl3): δ 7.45 (d, J=8.5 Hz, 2H), 7.33 (t, J=8.5 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 4.00 (s, 6H).

후처리

  1. temperatureThe mixture was then heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (4×50 mL)
  5. customAfter drying under vacuum
  6. temperaturethe solid was heated
  7. temperatureat reflux in ethanol (300 mL) for 2 hours
  8. temperatureAfter cooling to room temperature
  9. filtrationthe desired product was then collected by filtration

출처 및 근거

ORD 기록
ord-d495cc15923b4cdcbbd5c28f1c784c6f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035004B2

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