反应 #1148656

反应方程式

epichlorohydrin

potassium hydroxide

sodium sulfate

→

glycidyl ether

收率 63.0%

反应条件

后处理

1. 1
   workup.ADDITION) were added to a 50 ml 3-neck round bottom flask
2. 2
   其他equipped
3. 3
   温度with reflux condenser
4. 4
   其他thermometer and mechanical stirrer to form a reaction mixture
5. 5
   workup.STIRRINGWhile the reaction mixture was stirring
6. 6
   温度with a temporary cooling of the reaction mixture to 20-25° C.
7. 7
   workup.ADDITIONto each addition
8. 8
   其他After termination of the reaction
9. 9
   温度the mixture was cooled to room temperature
10. 10
    过滤filtered
11. 11
    workup.ADDITIONThe organic part of the mixture was treated with diethylether
12. 12
    洗涤washed with distilled water until the wash water
13. 13
    干燥After the organic solution was dried over anhydrous magnesium sulfate
14. 14
    workup.ADDITIONtreated with activated charcoal
15. 15
    过滤filtered
16. 16
    其他the solvent was removed
17. 17
    其他The residue was purified by column chromatography (silica gel, grade 62, 60-200 mesh, 150 Å, Aldrich)
18. 18
    workup.ADDITIONa mixture of acetone
19. 19
    workup.ADDITIONFractions containing the product
20. 20
    其他were collected
21. 21
    其他the solvent was evaporated

实验过程

A 6.8 g (14 mmol) quantity of 1,3-bis(4,4′-dimethyl-diphenylamino)-4-hydroxybenzene and 32 ml (0.4 mol) of epichlorohydrin (commercially obtained from Aldrich, Milwaukee, Wis.) were added to a 50 ml 3-neck round bottom flask equipped with reflux condenser, thermometer and mechanical stirrer to form a reaction mixture. The reaction mixture was stirred vigorously at 35-40° C. for 7 hours. While the reaction mixture was stirring, 2.7 g (0.04 mol) of powdered 85% potassium hydroxide and 0.7 g (5 mmol) of anhydrous sodium sulfate were added in two portions, with a temporary cooling of the reaction mixture to 20-25° C. prior to each addition. After termination of the reaction, the mixture was cooled to room temperature and filtered. The organic part of the mixture was treated with diethylether and washed with distilled water until the wash water had a neutral pH. After the organic solution was dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered, the solvent was removed. The residue was purified by column chromatography (silica gel, grade 62, 60-200 mesh, 150 Å, Aldrich) using a mixture of acetone:hexane in a volume ratio of 1:4 as the eluant. Fractions containing the product were collected and the solvent was evaporated to afford 4.8 g (63%) of glycidyl ether of 1,3-bis(4,4′-dirnethyldiphenylamino)phenol (Compound 2). A 1H NMR spectrum (250 MHz, CDCl3) yielded chemical shifts, in ppm, of: 7.05-6.70 (m, 19H, Ar); 3.84 (d, J=4.0 Hz, OCH2); 2.84 (m, 1H, CH); 2.33 (dd, 1H, one of CH2 of oxirane); and 2.27 (s, 12H, CH3). An elemental analysis resulted in the following values in weight %: C 82.08; H 6.61; N 5.07, which compared with calculated values for C37H36N2O2 in weight percent of: C82.19; H 6.71; N 5.18.

来源