4-Cyclohexylresorcinol → 1,3-Dioxo-6-cyclohexyl-cyclohexane

HRID 980826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980826
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([OH:11])=[CH:9][C:8]=2[OH:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[OH-].[Na+].[Ni]>[O:14]=[C:8]1[CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH2:12][C:10](=[O:11])[CH2:9]1

Komponenten

4

Edukt 1

HCID 750554-Cyclohexylresorcinol

Produkt 1

HCID 202209951,3-Dioxo-6-cyclohexyl-cyclohexaneAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

20.0 g (0.104 mol) of 4-cyclohexylresorcinol are dissolved in 40 ml of ten percent strength sodium hydroxide solution and are hydrogenated in the presence of 5 g of Raney nickel in an autoclave at 90° under 20 bar for 5 hours. The reaction mixture is rinsed out of the autoclave with alcohol. After removal of the catalyst, 100 ml of 90 percent strength acetic acid are slowly added to the solution. After addition of water, the reaction product crystallises out. It is dried in vacuo over NaOH. 12.9 g of 1,3-dioxo-6-cyclohexyl-cyclohexane of melting point 137°-140° C. are obtained. After recrystallisation from ethyl acetate, the product has a melting point of 142°-144° C. (literature). Yield: 11.1 g (=55%).

Aufarbeitung

  1. washThe reaction mixture is rinsed out of the autoclave with alcohol
  2. customAfter removal of the catalyst, 100 ml of 90 percent strength acetic acid
  3. additionare slowly added to the solution
  4. additionAfter addition of water
  5. customthe reaction product crystallises out
  6. dry with materialIt is dried in vacuo over NaOH

Quellen und Nachweise

ORD-Eintrag
ord-8fdfe03ebbbd4228a8bde573678a33a8
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04639453

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