반응 #5633

반응 방정식

resorcinol

KOH

KOH

KOH

1,8-dibromooctane

→

product

수율 27.0%

1,8-BIS(3-HYDROXYPHENOXY)OCTANE

수율 27.0%

용매

water

water

water

반응 조건

후처리

1. 1
   기타A five neck five liter round bottom flask equipped with a mechanical stirrer
2. 2
   기타two condensers, and a dropping funnel is purged with nitrogen
3. 3
   온도The easily stirable reaction mass is slowly heated
4. 4
   온도to reflux under a slow nitrogen
5. 5
   기타purge
6. 6
   온도at reflux under a nitrogen blanket over a period of two hours
7. 7
   workup.DISSOLUTIONthe reaction mass has dissolved to light tea colored solution
8. 8
   온도it becomes increasingly clouded as salt
9. 9
   기타is formed
10. 10
    workup.ADDITIONhas been added
11. 11
    기타The reaction is quenched with 1.5 liters of water
12. 12
    기타The reaction mixtures
13. 13
    여과filtered
14. 14
    기타to recover a tan colored solid which
15. 15
    세척to wash out resorcinol and KBr
16. 16
    여과The cooled slurry is then filtered
17. 17
    기타350 grams of crude product is recovered
18. 18
    기타Crystallization from 400 ml acetone yield 170 grams white crystals, 88%
19. 19
    기타pure by HPLC peak area, and recrystallization from 500 ml acetone

실험 절차

A five neck five liter round bottom flask equipped with a mechanical stirrer, two condensers, and a dropping funnel is purged with nitrogen then charged under a nitrogen blanket with 1.6 kg (14.5 moles) resorcinol, 160 grams deionized water, and 296.7 grams (1.091 moles) 1,8-dibromooctane. The easily stirable reaction mass is slowly heated to reflux under a slow nitrogen purge. A solution of 181 grams (2.74 moles) 85% KOH pellets in 184 grams water is added dropwise at reflux under a nitrogen blanket over a period of two hours. After about 25% of the KOH has been added, the reaction mass has dissolved to light tea colored solution then it becomes increasingly clouded as salt is formed. The reaction mixture is refluxed an additional hour after all the KOH has been added. The pH of the reaction mixture is basic. The reaction is quenched with 1.5 liters of water and acidified with 40% sulfuric acid. The reaction mixtures is then poured into 4 liters of water, cooled in an ice bath to a temperature of 10° C. and filtered to recover a tan colored solid which is slurried in 1.2 liters boiling water to wash out resorcinol and KBr. The cooled slurry is then filtered and 350 grams of crude product is recovered. Crystallization from 400 ml acetone yield 170 grams white crystals, 88% pure by HPLC peak area, and recrystallization from 500 ml acetone yields 97.4 grams product of 96% purity by HPLC peak area and high purity by gel permeation chromatography (m.p. 78°-82° C.).

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