Reacción #160687

Ecuación de reacción

potassium carbonate

4-chlorobenzyl chloride

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

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

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product

Rendimiento 73.6%

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

Rendimiento 73.6%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroExcess acetone was removed by rotary evaporation under reduced pressure
2. 2
   Otrothe resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N)
3. 3
   LavadoThe organic layer was washed with water and brine
4. 4
   Secadodried over magnesium sulphate
5. 5
   OtroEthyl acetate was removed by rotary evaporation under reduced pressure
6. 6
   Otroto afford the crude product
7. 7
   OtroThe crude oil was triturated with a 50/50 mixture of diethyl ether and hexane

Procedimiento

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).

Fuente