Reacción #160688

Ecuación de reacción

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

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

→

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

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux overnight
2. 2
   OtroExcess acetic acid was removed by rotary evaporation under reduced pressure (hard vacuum)
3. 3
   ExtracciónThe organic layer was extracted with aqueous sodium hydroxide solution (1 N; 3×150 mL)
4. 4
   Extracciónback extracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with brine
6. 6
   Secadodried over magnesium sulphate
7. 7
   OtroThe resulting oil was triturated with 50/50 diethyl ether/hexane
8. 8
   Filtraciónthe solid product 42 collected by vacuum filtration
9. 9
   Lavadothe precipitate washed with hexane (32.6 g, 44%, retention time 3.08 mins, ES− 261.33)

Procedimiento

A solution of 3-(4-chloro-benzyloxy)-4-(4-methoxy-benzyloxy)-benzaldehyde (41)(108 g) in acetic acid (500 mL) was heated at reflux overnight. Excess acetic acid was removed by rotary evaporation under reduced pressure (hard vacuum) and the resulting residue taken up in ethyl acetate. The organic layer was extracted with aqueous sodium hydroxide solution (1 N; 3×150 mL). The combined inorganic phases were neutralised with conc. hydrochloric acid and back extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulphate. The resulting oil was triturated with 50/50 diethyl ether/hexane, the solid product 42 collected by vacuum filtration and the precipitate washed with hexane (32.6 g, 44%, retention time 3.08 mins, ES− 261.33).

Fuente