1,4-Cyclohexanediol → 4-(Cyclohex-3-enylmethoxy)cyclohexanol

HRID 1015692

Reaktionsgleichung

Reaktionsgleichung von HRID 1015692
Cl[CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1.[CH:9]1([OH:16])[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:3]1([CH2:2][O:15][CH:12]2[CH2:13][CH2:14][CH:9]([OH:16])[CH2:10][CH2:11]2)[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1

Komponenten

6

Edukt 3

HCID 111621,4-CyclohexanediolHCID 14798Sodium HydroxideHCID 5569564-(Chloromethyl)cyclohexene

Produkt 1

HCID 667127934-(Cyclohex-3-enylmethoxy)cyclohexanolAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To toluene (500 g) were added 4-chloromethylcyclohexene (0.1 mol), 1,4-cyclohexanediol (0.5 mol), and tetrabutylammonium bromide (0.01 mol), and the mixture was heated to 90° C. and combined with a 5 N aqueous sodium hydroxide solution (100 g) added dropwise, followed by stirring for a for hours. The toluene solution (toluene layer) was washed with water, concentrated, purified by silica gel chromatography, and thereby yielded 13 g of 4-(cyclohex-3-enylmethoxy)cyclohexanol with a purity of 99%.

Aufarbeitung

  1. additionadded dropwise
  2. washThe toluene solution (toluene layer) was washed with water
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fc797e0ec39f412c9f72b8421f67e599
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985866B2

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