Réaction #631986

Équation de réaction

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

NEt3

dimethylamino pyridine

benzoylchloride

HCl

→

product

Rendement 77.2%

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

Rendement 77.2%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source