반응 #464076

반응 방정식

potassium carbonate

7-hydroxy-3,4-dihydro-2H-naphthalen-1-one

bromobenzene

→

7-phenoxy-3,4-dihydro-2H-naphthalen-1-one

수율 78.6%

용매

pyridine

반응 조건

후처리

1. 1
   온도The reaction mixture was heated for 4 days
2. 2
   온도under reflux
3. 3
   기타After evaporating the pyridine completely under vacuum
4. 4
   workup.STIRRINGthe residue was stirred with 200 ml ethyl acetate
5. 5
   여과was filtered through silica gel
6. 6
   세척The filtrate was washed with saturated solutions of ammonium chloride and sodium chloride
7. 7
   건조dried over sodium sulfate
8. 8
   농축concentrated by evaporation under vacuum
9. 9
   기타The residue was purified by column chromatography

실험 절차

A suspension of 60.8 g potassium carbonate in 300 ml of dry pyridine was treated with 35.7 g 7-hydroxy-3,4-dihydro-2H-naphthalen-1-one, and the mixture was heated to 40° C. Thereafter, 19.9 g copper(II) oxide was added thereto with stirring, followed by the drop-wise addition of 39.6 g bromobenzene. The reaction mixture was heated for 4 days under reflux. After evaporating the pyridine completely under vacuum, the residue was stirred with 200 ml ethyl acetate and was filtered through silica gel. The filtrate was washed with saturated solutions of ammonium chloride and sodium chloride, dried over sodium sulfate and concentrated by evaporation under vacuum. The residue was purified by column chromatography, using n-hexane/ethyl acetate as the elutant, whereupon 41.2 g (78.6% of theoretical) 7-phenoxy-3,4-dihydro-2H-naphthalen-1-one was obtained.

출처