反应 #2175420

反应方程式

Iodomethane

4-butyl-4′-hydroxyazobenzene

potassium carbonate

→

desired product

4-Butyl-4′-methoxyazobenzene

溶剂

acetone

acetone

反应条件

后处理

1. 1
   其他degassed with argon
2. 2
   workup.ADDITIONadded drop-wise to the stirred mixture
3. 3
   其他12 h
4. 4
   过滤The hot reaction mixture was then filtered
5. 5
   其他to remove the precipitated potassium iodide
6. 6
   其他The filtrate was collected
7. 7
   其他the solvent removed in vacuo
8. 8
   workup.DISSOLUTIONThe solid residue was re-dissolved in chloroform
9. 9
   其他insoluble salts were removed by filtration
10. 10
    洗涤The filtrate was washed with water
11. 11
    其他the organic layer was separated
12. 12
    干燥dried over magnesium sulfate
13. 13
    其他Removing the solvent in vacuo
14. 14
    其他afforded a solid

实验过程

All chemicals were obtained from Sigma-Aldrich Chemical Co. unless otherwise noted. One eq. of 4-butyl-4′-hydroxyazobenzene (obtained from Beam Corp.) and 1.1 eq. potassium carbonate were dissolved in acetone and degassed with argon. Iodomethane (2.5 eq) in acetone was degassed and added drop-wise to the stirred mixture. The mixture was heated to 45° C. and stirred overnight. The progress of the reaction was monitored by thin-layer chromatography (TLC); 12 h was usually sufficient for complete methylation. The hot reaction mixture was then filtered to remove the precipitated potassium iodide. The filtrate was collected and the solvent removed in vacuo. The solid residue was re-dissolved in chloroform and then insoluble salts were removed by filtration. The filtrate was washed with water, and the organic layer was separated and dried over magnesium sulfate. Removing the solvent in vacuo afforded a solid that contained the desired product (“BMAB”) containing a small amount of un-reacted starting material 4-butyl-4′-hydroxyazobenzene. Recrystallization from methanol at −68° C. afforded pure crystals of BMAB that were collected by filtration. (K 35 N 45 I) 1H NMR 200 MHz δ ppm=0.94 (t, 3H), 1.18 (q, 2H), 1.66 (q, 2H), 2.66 (t, 2H), 3.86 (s, 2H), 7.0 (d, 2H), 7.26 (d, 2H), 7.82 (d, 2H), 7.88 (d, 2H).

来源