Dimethyl Sulfate → 4-Hydroxy-4'-methoxybiphenyl

HRID 35985

Reaktionsgleichung

Reaktionsgleichung von HRID 35985
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.S(OC)(O[CH3:21])(=O)=O>O>[CH3:21][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 71124,4'-DihydroxybiphenylHCID 14798Sodium Hydroxide

Produkt 1

HCID 110308394-Hydroxy-4'-methoxybiphenylAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

120 ml of water and sodium hydroxide (14.00 g, 0.35 mol) were placed in a conical flask and dissolved. 4,4'-Dihydroxybiphenyl (28.00 g, 0.15 mol) was then added and heated to reflux for 2 hours with stirring using a condenser. Dimethyl sulfate (14.5 ml, 0.15 mol) was added dropwise over about 40 minutes. After addition, the mixture was heated while stirring for 2 hours, and then allowed to cool and filtrated. The filter cake was transferred into 700 ml of water, which was then heated to boiling temperature, and filtrated while still keeping warm. The filtrate was kept at 70° C., and 20% hydrochloric acid was added. White precipitation: formed was washed extensively. Recrystallization from ethanol yielded 4'-methoxy-4-hydroxybiphenyl (13.17 g, Yield: 48.0%).

Aufarbeitung

  1. dissolutiondissolved
  2. temperatureheated
  3. temperatureto reflux for 2 hours
  4. additionAfter addition
  5. temperaturethe mixture was heated
  6. stirringwhile stirring for 2 hours
  7. temperatureto cool
  8. filtrationfiltrated
  9. temperaturewas then heated
  10. filtrationfiltrated
  11. temperaturewhile still keeping warm
  12. customwas kept at 70° C.
  13. addition20% hydrochloric acid was added
  14. customWhite precipitation
  15. customformed
  16. washwas washed extensively
  17. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-22bc116db45d424b96b7e0d2b5e88843
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412079

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