Formaldehyde → 2-Methylenetetralin-1-one

To a suspension of paraformaldehyde (46.2 g, 1.54 mol) and N-methylanilinium trifluoroacetate (TAMA, 46.2 g, 1.54 mol) in 340 mL of dry THF was added α-tetralone (50 g, 0.342 mol). The solution was heated at reflux under nitrogen with stirring for 4 h, during which time the paraformaldehyde dissolved. After cooling, diethyl ether (700 mL) was added to the reaction mixture. The solvent was separated from the reaction mixture and washed with 500 mL of saturated sodium bicarbonate. Additional diethyl ether was added to the reaction mixture, separated and used to back extract the aqueous sodium bicarbonate layer. The combined organic layers were dried over magnesium sulfate, and the solution was then concentrated to a volume of approximately 300 mL and filtered through Celite. Complete evaporation of the ether yielded 50 g (90° A) of crude 2-methylene-3,4-dihydronaphthalen-1-one, which was used immediately for the next reaction to prevent polymerization of the product.

1. temperatureThe solution was heated
2. temperatureat reflux under nitrogen
3. dissolutiondissolved
4. temperatureAfter cooling
5. customThe solvent was separated from the reaction mixture
6. washwashed with 500 mL of saturated sodium bicarbonate
7. additionAdditional diethyl ether was added to the reaction mixture
8. customseparated
9. extractionto back extract the aqueous sodium bicarbonate layer
10. dry with materialThe combined organic layers were dried over magnesium sulfate
11. concentrationthe solution was then concentrated to a volume of approximately 300 mL
12. filtrationfiltered through Celite
13. customComplete evaporation of the ether

ORDレコード

ord-a19c461eeff2466083c28a8ef53ce8ee

出典データセット

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08603645B2