تفاعل #553430

معادلة التفاعل

4-heptanone

allylmagnesium bromide

allyl bromide

NH4Cl

HCl

→

4-hydroxy-4-propyl-1-heptene

المذيبات

diethyl ether

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition the mixture
2. 2
   درجة الحرارةwas refluxed for 10 hrs
3. 3
   أخرىThe ether phase was separated
4. 4
   استخلاصthe water phase extracted with diethyl ether (3×100 ml)
5. 5
   غسيلThe combined organic phases were then washed with a Na2CO3 -solution and water
6. 6
   تجفيفdried with Na2SO4
7. 7
   أخرىevaporated
8. 8
   workup.DISTILLATIONThe residue was distilled

الإجراء التجريبي

113 g of 4-heptanone in 1000 ml of dry diethyl ether was slowly added to a solution of allylmagnesium bromide, prepared from 36.5 g of Mg and 178 g of allyl bromide in 500 ml dry diethyl ether. After the addition the mixture was refluxed for 10 hrs. The reaction mixture was poured on a mixture of 150 g ice, 450 ml of 20% NH4Cl and 350 ml of 5M HCl. The ether phase was separated and the water phase extracted with diethyl ether (3×100 ml). The combined organic phases were then washed with a Na2CO3 -solution and water, dried with Na2SO4 and evaporated. The residue was distilled. Yield: 142 g (b.p. 38°-40° C./0.1 torr) 1H-NMR(CDCl3): δ0.9(6H,CH3), 1.3-1.6(9H,CH2,OH), 2.1-2.3 (CH2C=C), 5.0-5.2(CH2 =C), 5.6-6.1 (CH=C)

المصدر