Acetone → 1,7-Dimethoxynaphthalene

HRID 2210007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2210007
[CH3:1]C(C)=O.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13](O)[CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O>[CH3:1][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:17])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 68462Naphthalene-1,7-diol

Produkt 1

HCID 791971,7-DimethoxynaphthaleneAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To one liter of acetone were added 50.0 grams (0.31 mole) of 1,7-dihydroxynaphthalene. To the solution then were added 95.0 gm (0.69 mole) of powdered potassium carbonate and 65 mL (0.69 mole) of dimethyl sulfate. The reaction mixture was stirred at reflux under nitrogen for 18 hours. The reaction mixture then was cooled to room temperature and diluted with 2 L of water. The mixture was then extracted with dichloromethane. The organic extracts were combined, washed successively with water and saturated aqueous sodium chloride, dried over sodium sulfate and evaporated in vacuo to give a brown oil. The oil was distilled in vacuo to give 52.51 gm (90.1%) of 1,7-dimethoxynaphthalene as a light orange, transparent oil, b.p.=115°-157° C. (4 mm Hg).

Aufarbeitung

  1. temperatureat reflux under nitrogen for 18 hours
  2. extractionThe mixture was then extracted with dichloromethane
  3. washwashed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give a brown oil
  7. distillationThe oil was distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ec567e58200403e9f4ce1f80befb2f5
Quelldatensatz
uspto-grants-1995_10
Patentnummer
US05457121

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