تفاعل #514061

معادلة التفاعل

6-(4-hydroxyphenyl)hexyl bromide

6-(4-methoxyphenyl)hexyl bromide

potassium iodide

3,5-heptanedione

potassium carbonate

boron tribromide

→

4-[6-(4-hydroxyphenyl)hexyl]-3,5-heptanedione

المذيبات

methylene dichloride

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 24 hours
2. 2
   workup.DISTILLATIONOne liter of solvent is distilled off
3. 3
   workup.ADDITIONthe remainder of the reaction mixture is poured
4. 4
   workup.STIRRINGwith stirring into a solution of 4 liters of ice-water containing 160 ml
5. 5
   استخلاصThe separated product is extracted with ether
6. 6
   غسيلthe ether extracts washed with saturated sodium chloride solution
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe ether is distilled off in vacuo
9. 9
   أخرىthe excess 3,5-heptanedione removed at 70° C. (0.8 mm.)
10. 10
    أخرىin a rotary evaporator
11. 11
    أخرىThe residual product is crystallized from isopropyl alcohol-pentane

الإجراء التجريبي

A suspension of 0.5 mole of 6-(4-hydroxyphenyl)hexyl bromide [pepared from 6-(4-methoxyphenyl)hexyl bromide and boron tribromide in methylene dichloride according to the procedure of Example 42f], 0.125 mole of potassium iodide, 1.15 moles of 3,5-heptanedione and 1.05 moles of powdered anhydrous potassium carbonate (dried in vacuo for two hours) in 2 liters of acetone is stirred at reflux for 24 hours. One liter of solvent is distilled off and the remainder of the reaction mixture is poured with stirring into a solution of 4 liters of ice-water containing 160 ml. of concentrated hydrochloric acid. The separated product is extracted with ether and the ether extracts washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The ether is distilled off in vacuo and the excess 3,5-heptanedione removed at 70° C. (0.8 mm.) in a rotary evaporator. The residual product is crystallized from isopropyl alcohol-pentane to give 4-[6-(4-hydroxyphenyl)hexyl]-3,5-heptanedione.

المصدر