1,2-Butanediol → 2-tert-Butylcyclohexyloxybutanol

HRID 1757684

Reaktionsgleichung

Reaktionsgleichung von HRID 1757684
[C:1]([CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][C:6]21[O:10][CH:9]([CH2:11][CH3:12])[CH2:8][O:7]2)([CH3:4])([CH3:3])[CH3:2].C(C1CCCCC1=O)(C)(C)C.C(O)C(O)CC>[Pd].C(O)(C)C>[C:1]([CH:5]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:6]1[O:7][CH2:8][CH:9]([OH:10])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 114291,2-ButanediolHCID 1026812-tert-ButylcyclohexanoneHCID 157895866-t-Butyl-2-ethyl-1,4-dioxaspiro[4.5]decane

Produkt 1

HCID 1644222-tert-ButylcyclohexyloxybutanolAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A 500 ml capacity autoclave was charged with 30 g (0.13 mol) of 6-t-butyl-2-ethyl-1,4-dioxaspiro[4.5]decane which has been prepared from 2-t-butylcyclohexanone and 1,2-butanediol, 150 g of isopropanol and 0.3 g of a catalyst of 5% palladium supported on active carbon (pH=7.6). The reaction was carried out under a hydrogen pressure of 70 kg/cm2 and at a temperature of 190° C. for 20 hours until completion of the absorption of hydrogen. After the reaction, the catalyst was removed by filtration and the resulting filtrate was subjected to distillation to obtain 24.2 g of 1-(2-t-butylcyclohexyloxy)-2-butanol (b.p.=122° to123° C./5 mmHg; yield=80%; cis:trans=66:34).

Aufarbeitung

  1. customat a temperature of 190° C. for 20 hours until completion of the absorption of hydrogen
  2. customAfter the reaction
  3. customthe catalyst was removed by filtration
  4. distillationthe resulting filtrate was subjected to distillation

Quellen und Nachweise

ORD-Eintrag
ord-32c3b9562e9942f6a1f53283c829a1d7
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446208

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