Réaction #631988

Équation de réaction

HCl

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

NEt3

tosylchloride

→

product

Rendement 50.0%

1-methyl-3-oxo-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)propyl 4-methyl-benzenesulfonate

Rendement 50.0%

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)

Mode opératoire

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (1.00 g, 92% pure, 4.38 mmol), DMAP (100 mg), and NEt3 (1.0 ml, 7.2 mmol) in CH2Cl2 (20 ml) was added, at 0° C., tosylchloride (2.02 g, 10.56 mmol). The reaction medium was stirred at room temperature for 4 days. Then, the mixture was acidified with concentrated 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). 0.76 g of product were thus obtained (yield: 50%).

Source