Реакция #631988

Уравнение реакции

HCl

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

NEt3

tosylchloride

→

product

Выход 50.0%

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

Выход 50.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Экстракцияextracted twice with ether
2. 2
   Промывкаwashed with water, saturated aqueous NaHCO3
3. 3
   СушкаFinally, the organic phases were dried over Na2SO4
4. 4
   Концентрированиеconcentrated at 50-60°/0.03 mbar)

Методика

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%).

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