Ammonium Chloride → 6-Ethyl-4'-(1-ethyl-1-hydroxypropyl)-2'-propylbiphenyl-3-ol

HRID 1869727

Reaktionsgleichung

Reaktionsgleichung von HRID 1869727
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH2:20][CH2:21][CH3:22])[CH3:2].[CH2:23]([Mg]Br)[CH3:24].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.O>[CH2:1]([C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH2:23][CH3:24])([OH:19])[CH2:17][CH3:18])=[CH:12][C:11]=2[CH2:20][CH2:21][CH3:22])=[CH:5][C:6]([OH:9])=[CH:7][CH:8]=1)[CH3:2]

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 223456391-(2'-Ethyl-5'-hydroxy-2-propylbiphenyl-4-yl)-1-propanoneHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 117168456-Ethyl-4'-(1-ethyl-1-hydroxypropyl)-2'-propylbiphenyl-3-olAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

370 g (1.248 mol) of 1-(2′-ethyl-5′-hydroxy-2-propylbiphenyl-4-yl)propan-1-one in solution in 3.7 liters of tetrahydrofuran are placed in a reactor. 915 ml of a 3M solution of ethylmagnesium bromide in ethyl ether are slowly run into this solution cooled to −10° C. At the end of the addition, the reaction mixture is kept stirred for 1 hour and then transferred onto 5 liters of a 2.5 molar solution of ammonium chloride in water. The organic phase is separated by settling and washed twice with 800 ml of water. After evaporating under reduced vacuum, the residue is dissolved with 2.75 liters of methylene chloride at reflux. The medium is allowed to return to ambient temperature with stirring and is then cooled to 5° C. The crystals are filtered off and then dried under vacuum. 260 g (64%) of 6-ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-propylbiphenyl-3-ol are obtained. Melting point: 130° C. 1H NMR (d6-DMSO) (ppm): 0.67-0.74, m, 9H; 0.9, t, 3H; 1.38, m, 2H; 1.71-1.77, m, 4H; 2.13-2.35, m, 4H; 4.48, s, 1H; 6.45, d, 1H; 6.70, dd, 1H; 6.94, d, 1H; 7.07, d, 1H; 7.18, dd, 1H; 7.26, s, 1H; 9.16, s, 1H

Aufarbeitung

  1. additionAt the end of the addition
  2. customThe organic phase is separated
  3. washwashed twice with 800 ml of water
  4. customAfter evaporating under reduced vacuum
  5. dissolutionthe residue is dissolved with 2.75 liters of methylene chloride
  6. temperatureat reflux
  7. customto return to ambient temperature
  8. stirringwith stirring
  9. temperatureis then cooled to 5° C
  10. filtrationThe crystals are filtered off
  11. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-84907fc26de94815b70d44f254242640
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638657B2

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