반응 #64234

반응 방정식

7,8-dihydroxy-1-octene

p-anisylchlorodiphenylmethane

water

→

8-hydroxy-7-methoxy-1-octene

수율 45.8%

용매

pyridine

반응 조건

후처리

1. 1
   추출extracted with ether
2. 2
   건조The ether solution was dried
3. 3
   기타evaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide
5. 5
   workup.ADDITIONthis solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period
6. 6
   workup.ADDITIONwas poured into water
7. 7
   추출extracted with ether
8. 8
   건조The ether solution was dried
9. 9
   기타evaporated
10. 10
    workup.DISSOLUTIONThe residue was dissolved in 400 ml of methanol
11. 11
    workup.STIRRINGstirred with 35 g of Amberlyst 15 resin
12. 12
    여과The solution was filtered
13. 13
    기타solvent was removed
14. 14
    기타The residue was purified by chromatography

실험 절차

A mixture of 45 g of 7,8-dihydroxy-1-octene and 101.2 g of p-anisylchlorodiphenylmethane in 200 ml of pyridine was allowed to stand at 10° C. for 48 hours. The mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 300 ml of dimethylformamide containing 83.1 ml of methyl iodide and this solution was added dropwise to a suspension of 17.75 g of 60t sodium hydride in 500 ml of dimethylformamide over a 2 hour period. After stirring an additional 13 hours the mixture was poured into water and extracted with ether. The ether solution was dried and evaporated. The residue was dissolved in 400 ml of methanol and stirred with 35 g of Amberlyst 15 resin. The solution was filtered and solvent was removed. The residue was purified by chromatography giving 22.6 g of 8-hydroxy-7-methoxy-1-octene as an oil.

출처