반응 #160687

반응 방정식

potassium carbonate

4-chlorobenzyl chloride

3-hydroxy-4-(4-methoxy-benzyloxy)-benzaldehyde

3-Hydroxy-4-(4-methoxy-benzyloxy)-benzaldehyde

→

product

수율 73.6%

3-(4-Chloro-benzyloxy)-4-(4-methoxy-benzyloxy)-benzaldehyde

수율 73.6%

용매

acetone

반응 조건

후처리

1. 1
   기타Excess acetone was removed by rotary evaporation under reduced pressure
2. 2
   기타the resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N)
3. 3
   세척The organic layer was washed with water and brine
4. 4
   건조dried over magnesium sulphate
5. 5
   기타Ethyl acetate was removed by rotary evaporation under reduced pressure
6. 6
   기타to afford the crude product
7. 7
   기타The crude oil was triturated with a 50/50 mixture of diethyl ether and hexane

실험 절차

A solution of 4-chlorobenzyl chloride (67.9 g), 3-hydroxy-4-(4-methoxy-benzyloxy)-benzaldehyde (40) (99 g) and tetrabutylammonium iodide (14.1 g) was heated at reflux in acetone (0.4 L) over solid potassium carbonate (39.1 g) for 3 hours. Excess acetone was removed by rotary evaporation under reduced pressure and the resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N). The organic layer was washed with water and brine and then dried over magnesium sulphate. Ethyl acetate was removed by rotary evaporation under reduced pressure to afford the crude product. The crude oil was triturated with a 50/50 mixture of diethyl ether and hexane accompanied by vigorous stirring to afford the product as a colourless solid (108 g, 73% yield, retention time 3.70 mins, poor ionization, ES− m/z 538.05). 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 7.51-7.43 (m, 2H), 7.42-7.32 (m, 6H), 7.07 (d, J=8.1 Hz, 1H), 6.97-6.89 (m, 2H), 5.19 (s, 2H), 5.17 (s, 2H), 3.85 (s, 3H).

출처