반응 #5630

반응 방정식

KOH

resorcinol

sulfuric acid

1,4-dibromobutane

→

1,4-BIS(3-HYDROXYPHENOXY)BUTANE

용매

water

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 reaction slurry is slowly heated
4. 4
   온도to reflux under a slow nitrogen
5. 5
   기타purge
6. 6
   온도After an additional hour of refluxing
7. 7
   workup.ADDITIONto pour the contents into 10 liters
8. 8
   여과before filtering under reduced pressure
9. 9
   세척washing with several portions of warm water
10. 10
    추출The residue, 80 grams of yellow amorphous solid, is then extracted with large quantities of boiling water
11. 11
    기타to remove oils
12. 12
    기타Recrystallization from acetone yielded product of >98% purity by HPLC analysis with a melting point of 103° C.-106° C. (literature melting point, 105° C.-108° C.) for use in examples 10, 18 and 20

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 1.5 kg (13.6 moles) resorcinol, 120 grams deionized water, and 138.75 grams (0.64 moles) 1,4-dibromobutane. The reaction slurry is slowly heated with stirring to reflux under a slow nitrogen purge; then a solution of 109 grams (1.64 moles) 85% KOH pellets in 109 grams water is added dropwise under a nitrogen blanket over a two hour period. After an additional hour of refluxing, the reaction mixture is allowed to coil enough to pour the contents into 10 liters deionized water. The water slurry is acidified with 30% sulfuric acid and allowed to stand at room temperature overnight before filtering under reduced pressure and washing with several portions of warm water. The residue, 80 grams of yellow amorphous solid, is then extracted with large quantities of boiling water to remove oils. After cooling to room temperature, the water extracts (14 liters) yield 28 grams of white, shiny platelets. HPLC analysis reveals 92% purity by peak area. Recrystallization from acetone yielded product of >98% purity by HPLC analysis with a melting point of 103° C.-106° C. (literature melting point, 105° C.-108° C.) for use in examples 10, 18 and 20. Both 1H and 13C NMR spectra are consistent with the proposed structure.

출처