反应详情

11-Chloromethyl-9,10-dihydro-9,10-ethanoanthracene (45 gm) was combined with 2-hydroxyethylmethylamine (45 gm) in xylene (300 ml) and the mixture heated to reflux for 17 days. The mixture was cooled to room temperature and extracted with 1 N hydrochloric acid (3×100 ml). The combined acid solutions were washed with ether (100 ml), made basic with the addition of 50% sodium hydroxide solution and the mixture extracted with ether (3×100 ml). The combined ether solutions were dried over magnesium sulfate and the ether removed on a rotary evaporator. The residue was distilled (220° C. at 7 mm Hg) to yield a colorless oil. The material was dissolved in ether (200 ml) and treated with 6 N hydrochloric acid in isopropyl alcohol (2 ml). The resulting precipitate was filtered and washed with ether to provide the product. Analytical data are reported in Table I.

1. temperaturethe mixture heated
2. temperatureto reflux for 17 days
3. extractionextracted with 1 N hydrochloric acid (3×100 ml)
4. washThe combined acid solutions were washed with ether (100 ml)
5. additionmade basic with the addition of 50% sodium hydroxide solution
6. extractionthe mixture extracted with ether (3×100 ml)
7. dry with materialThe combined ether solutions were dried over magnesium sulfate
8. customthe ether removed on a rotary evaporator
9. distillationThe residue was distilled (220° C. at 7 mm Hg)
10. customto yield a colorless oil
11. filtrationThe resulting precipitate was filtered
12. washwashed with ether
13. customto provide the product