Sodium Bicarbonate → 3-[2-Hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-one

HRID 1074469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074469
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+].[H][H]>[Pd].C(O)C>[CH3:23][C:15]([C:13]1[CH:12]=[CH:11][C:10]([CH:24]2[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]2)=[C:9]([OH:8])[CH:14]=1)([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 127881893-[2-(Benzyloxy)-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 127881913-[2-Hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 19.5 g. (0.0468 mol.) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]cyclohexanone, 12.3 g. of sodium bicarbonate, 3.00 g. of 10% palladium-on-carbon and 250 ml. of ethanol was stirred under one atmosphere of hydrogen pressure for 1.5 hours. The reaction mixture was then filtered through diatomaceous earth with ethyl acetate and the filtrate evaporated to a solid. The crude solid was purified via column chromatography on 280 g. of silica gel eluted with 20% ethercyclohexane to yield a solid. Recrystallization of this sold from aqueous methanol gave 9.1 g. (62%) of the title product, m.p. 87° C., principally in the hemiketal form.

Aufarbeitung

  1. additionA mixture of 19.5 g
  2. filtrationThe reaction mixture was then filtered through diatomaceous earth with ethyl acetate
  3. customthe filtrate evaporated to a solid
  4. customThe crude solid was purified via column chromatography on 280 g
  5. washof silica gel eluted with 20% ethercyclohexane
  6. customto yield a solid
  7. customRecrystallization of
  8. customgave 9.1 g

Quellen und Nachweise

ORD-Eintrag
ord-975a8f40874b44358d9da6bb1e05f49d
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04391827

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