Реакция #63245

Уравнение реакции

2-propyl-3,4-dichlorophenol

potassium iodide

sodium hydride

6bromohexanoic acid

→

title compound

6-(2-propyl-3,4-dichlorophenoxy)hexanoic acid

Растворители

water

ethyl acetate

hexamethylphosphoramide

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONTo the solution were then added 1.3 g
2. 2
   ДругоеThe solution was evaporated to dryness
3. 3
   workup.ADDITIONFresh ethyl acetate and water were added
4. 4
   Другоеthe layers were separated
5. 5
   workup.ADDITIONFresh ethyl acetate was added to the aqueous layer
6. 6
   ДругоеThe layers were separated
7. 7
   Промывкаthe organic layer was washed with a saturated sodium chloride solution
8. 8
   ФильтрацияThe organic layer was then filtered through sodium sulfate
9. 9
   Другоеevaporated to dryness
10. 10
    ЭкстракцияThe resulting residue was extracted with hexane
11. 11
    Другоеevaporated to dryness
12. 12
    Другоеto afford 500 mg

Методика

To a solution of 1.1 g. of 2-propyl-3,4-dichlorophenol in 30 ml. of tetrahydrofuran and 30 ml. of hexamethylphosphoramide were added 4.1 g. of 6bromohexanoic acid. To the solution were then added 1.3 g. of a 50% oil dispersion of sodium hydride. A catalytic amount of potassium iodide was added and the reaction was stirred under a nitrogen atmosphere at 60°-70° C. overnight. The reaction was cooled to room temperature and ethyl acetate and water were added. The solution was evaporated to dryness. Fresh ethyl acetate and water were added and the layers were separated. Fresh ethyl acetate was added to the aqueous layer and the aqueous layer was adjusted to pH 2. The layers were separated and the organic layer was washed with a saturated sodium chloride solution. The organic layer was then filtered through sodium sulfate and evaporated to dryness. The resulting residue was extracted with hexane and evaporated to dryness to afford 500 mg. of the title compound.

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