Reaktion #631986

Reaktionsgleichung

3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

NEt3

dimethylamino pyridine

benzoylchloride

HCl

→

product

Ausbeute 77.2%

1-methyl-3-oxo-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)propyl Benzoate

Ausbeute 77.2%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted twice with ether
2. 2
   Waschenwashed with water, saturated aqueous NaHCO3
3. 3
   TrocknenFinally, the organic phases were dried over Na2SO4
4. 4
   Einengenconcentrated at 50-60°/0.03 mbar) and
5. 5
   Sonstigepurified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3)

Vorschrift

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (4.00 g, 92% pure, 17.5 mmol), NEt3 (3.2 ml, 22.85 mmol) and dimethylamino pyridine (DMAP) (400 mg) in CH2Cl2 (100 ml) was added benzoylchloride (2.43 ml, 20.94 mmol). The reaction medium was stirred for 65 h at room temperature. Then, the mixture was acidified with 5% aqueous HCl and extracted twice with ether and washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl. Finally, the organic phases were dried over Na2SO4, concentrated at 50-60°/0.03 mbar) and purified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3). 4.25 g of product were thus obtained (yield: 73%).

Quelle