Reaktion #631988

Reaktionsgleichung

HCl

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

NEt3

tosylchloride

→

product

Ausbeute 50.0%

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

Ausbeute 50.0%

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)

Vorschrift

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%).

Quelle