反应详情

The nitrogen-purged apparatus described in Example 17A for the preparation of DCPSeb was charged with 300 ml of molecular sieves-dried pyridine and 20.3 g of terephthaloyl chloride (0.10 moles, MW=203.0, Aldrich, 97%), which gave a cloudy, yellow mixture. A solution of 32.6 g of 2,4-dichlorophenol (0.20 moles) in 100 ml of dry pyridine was dripped into the stirred mixture over 15 min, causing a 1.3° C. exotherm. The mixture thickened and turned white. It was stirred 6 h more and left unstirred overnight. The mixture was slightly acidified with 10% aq HCl, the crude product isolated from it by vacuum filtration, then rinsed twice with ethanol on the funnel and dried on the funnel to 62 g of slightly wet solid. The product gave a hazy solution in 1200 ml of hot THF, which was filtered hot. After 2 h, a first crop of recrystallized solid was isolated by vacuum filtration and rinsed with a minimum of THF. More solids appeared in the filtrate after concentration to 200 ml. A second crop was taken as above after crystallization. The 2 crops were dried on their respective filtration funnels and then overnight at room temPerature in a vacuum oven with a slight nitrogen bleed. The combined weight, 27.1 g, was 60% of the theoretical 45.6 g. Elemental analysis is consistent with theory. Calcd. for C20H10O4Cl4 : C, 52.7; H, 2.2; Cl, 31.1. Found: C, 52.8; H. 2.2; Cl, 31.5.

1. customThe nitrogen-purged apparatus
2. customdescribed in Example 17A for the preparation of DCPSeb
3. customgave a cloudy, yellow mixture
4. customcausing a 1.3° C.
5. waitleft unstirred overnight
6. customthe crude product isolated from it by vacuum filtration
7. washrinsed twice with ethanol on the funnel
8. customdried on the funnel to 62 g of slightly wet solid
9. customThe product gave a hazy solution in 1200 ml of hot THF
10. filtrationwhich was filtered hot
11. waitAfter 2 h
12. customa first crop of recrystallized solid was isolated by vacuum filtration
13. washrinsed with a minimum of THF
14. concentrationafter concentration to 200 ml
15. customafter crystallization
16. customThe 2 crops were dried on their respective filtration funnels
17. customovernight
18. customat room temPerature