反应详情

Into a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet, was placed 10 g (52 mmoles) of 6-amino-2,4-dichloro-3-methylphenol and 150 ml of ethyl acetate. With stirring a solution resulted. To this solution was added 4.53 g (57.2 mmoles) of pyridine. This solution was stirred for 5 minutes during which time 10.95 g (54.6 mmoles) of 3,5-dimethoxybenzoyl chloride (Aldrich Chemical Co., CAS RN 17213-57-9) was dissolved in 75 ml of ethyl acetate and placed in an addition funnel. This solution was added dropwise to the reaction vessel over a 30 minute period. A precipitate formed almost immediately. After complete addition the reaction mixture was allowed to stir overnight. Thin layer chromatography (5/95 acetone/CH2Cl2) analysis of the reaction mixture indicated no starting material and primarily one new spot and a spot at the origin. The reaction mixture was poured into a separatory funnel and washed 2 times with a cold 10% hydrochloric acid solution followed by 2 times with a saturated sodium chloride solution and the organic layer was dried over sodium sulfate. The sodium sulfate was collected on a gravity filter and the filtrate was concentrated to a salmon colored solid. This solid was recrystallized from refluxing ethanol. The resulting crystals were collected on a medium sintered glass funnel, and dried by sucking air through for three hours. 8.9 g of desired product was obtained, a 48% purified yield.

1. customInto a 500 ml 3-necked round bottom flask, equipped with a stir bar, addition funnel, and N2 inlet
2. customresulted
3. customplaced in an addition funnel
4. additionThis solution was added dropwise to the reaction vessel over a 30 minute period
5. customA precipitate formed almost immediately
6. additionAfter complete addition the reaction mixture
7. stirringto stir overnight
8. additionThe reaction mixture was poured into a separatory funnel
9. washwashed 2 times with a cold 10% hydrochloric acid solution
10. dry with materialthe organic layer was dried over sodium sulfate
11. customThe sodium sulfate was collected on a gravity
12. filtrationfilter
13. concentrationthe filtrate was concentrated to a salmon
14. customThis solid was recrystallized
15. temperaturefrom refluxing ethanol
16. customThe resulting crystals were collected on a medium sintered glass funnel
17. customdried
18. customthrough for three hours