Potassium Carbonate → Benzenemethanol, 4-chloro-alpha-ethyl-alpha-(4-((6-methyl-2-pyridinyl)methoxy)phenyl)-

HRID 745221

Reaktionsgleichung

Reaktionsgleichung von HRID 745221
[CH2:1]([C:3]([OH:18])([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[N:27]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)([OH:18])[CH2:1][CH3:2])=[CH:9][CH:8]=2)[N:27]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 765462-(Chloromethyl)-6-methylpyridineHCID 14727318alpha-Ethyl-alpha-(4-chlorophenyl)-4-hydroxy-benzylalcohol

Produkt 1

HCID 3022025Benzenemethanol, 4-chloro-alpha-ethyl-alpha-(4-((6-methyl-2-pyridinyl)methoxy)phenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

13.1 g. of α-ethyl-α-(4-chlorophenyl)-4-hydroxybenzyl-alcohol, 14 g. of anhydrous potassium carbonate, 0.85 g. of tetrabutylammonium hydrogensulfate and 7.8 g. of 2-methyl-6-chloromethyl-pyridine in 140 ml. of ethyl acetate are boiled for 18 hours. The solvent is distilled off under reduced pressure, to the residue water is added, and it is extracted with ether. The ethereal solution is washed to neutral with a 5% aqueous potassium hydroxide solution and subsequently water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Crystallization of the residue from a mixture of hexane and ethyl acetate yields 13.6 g. of the title compound, melting at 100° to 101° C.

Aufarbeitung

  1. distillationThe solvent is distilled off under reduced pressure, to the residue water
  2. additionis added
  3. extractionit is extracted with ether
  4. washThe ethereal solution is washed to neutral with a 5% aqueous potassium hydroxide solution and subsequently water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customCrystallization of the residue
  8. additionfrom a mixture of hexane and ethyl acetate
  9. customyields 13.6 g

Quellen und Nachweise

ORD-Eintrag
ord-2be7deb7c5794779bbdbc1444ceead4d
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04598080

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