反应详情

To a 3-neck flask fitted with a mechanical stirrer, 600 mL of pyridine (dried over molecular sieve), 100 g of 4-bromo-1-methylnaphthalene, 55.6 g of phenol, 83.7 g of potassium carbonate, 14.9 g of copper(I)chloride, and 2 g copper bronze was added. Under a nitrogen atmosphere, the mixture was refluxed for 72 hours with vigorous stirring. The reaction mixture was cooled and poured into cold dilute hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed two times with cold dilute hydrochloric acid, dried over sodium sulfate, and filtered. After removing the solvent under vacuum, the product was flash chromatographed over silica gel with hexane elution. The product was further purified through fractional distillation, obtaining 35 g (33%) of the desired 1-methyl-4-phenoxynaphthalene intermediate at 150° C. at 0.075 torr.

1. customTo a 3-neck flask fitted with a mechanical stirrer
2. temperatureUnder a nitrogen atmosphere, the mixture was refluxed for 72 hours with vigorous stirring
3. temperatureThe reaction mixture was cooled
4. extractionthe resulting mixture was extracted with ethyl acetate
5. washThe organic layer was washed two times with cold dilute hydrochloric acid
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customAfter removing the solvent under vacuum
9. customchromatographed over silica gel with hexane elution
10. distillationThe product was further purified through fractional distillation