Methyl Ethyl Ketone → 3-Ethoxy-4-(2-bromoethoxy)benzyl alcohol

While stirring a mixture of 30 g of 3-ethoxy-4-hydroxybenzyl alcohol, 125 g of anhydrous potassium carbonate, and 600 ml of methyl ethyl ketone, 168 g of 1,2-dibromoethane was added to the mixture, and the resultant mixture was refluxed for 48 hours with stirring. After cooling, the reaction mixture was filtered under suction and the filtrate was distilled under reduced pressure to provide a pale-yellow oily matter. The product was dissolved in 300 ml of ether and the solution was washed twice each with 50 ml of an aqueous 5% sodium hydroxide solution and then with 50 ml of water, dried with anhydrous sodium sulfate, and distilled under reduced pressure to provide a yellow oily matter. To the product was added 100 ml of a mixture of ether and petroleum ether of 1:1 by volume ratio to form crystals, which were recovered by filtration under suction to provide 39 g of 3-ethoxy-4-(2-bromoethoxy)benzyl alcohol having a melting point of 51°-53° C.

1. additionwas added to the mixture
2. stirringwith stirring
3. temperatureAfter cooling
4. filtrationthe reaction mixture was filtered under suction
5. distillationthe filtrate was distilled under reduced pressure
6. customto provide a pale-yellow oily matter
7. washthe solution was washed twice each with 50 ml of an aqueous 5% sodium hydroxide solution
8. dry with materialwith 50 ml of water, dried with anhydrous sodium sulfate
9. distillationdistilled under reduced pressure
10. customto provide a yellow oily matter
11. customto form crystals, which
12. filtrationwere recovered by filtration under suction

ORDレコード

ord-1e0cf119f1a54d89993c78493263f005

出典データセット

uspto-grants-1980_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04217305