3-ethoxy-4-phenylmethoxybenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Benzyloxy-3-ethoxy-benzaldehyde (20 g) was dissolved in dichloromethane (100 ml) and a solution of nitric acid in dichloromethane (2M, 200 ml) was gradually added at a temperature under 30° C. The solution was stirred at room temperature for 10 min and then it was poured into ice-cold water. The organic phase was washed with 1M sodium hydroxide and water and then it was dried and evaporated. it was poured into ice-cold water The organic phase was washed with 1M sodium hydroxide and water it was dried evaporated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the solution of 3-ethoxy-4-hydroxy-benzaldehyde (83 g) in N,N-dimethylformamide (400 ml) was gradually added 10 M sodium hydroxide (55 ml) and then benzyl chloride (60 ml) was added at a temperature under 40° C. The mixture was stirred at room temperature for a half an hour and for 2 hours at 60° C. The solution was poured into ice-cold water (2 l) and extracted with diethyl ether. The organic phase was washed with water and 5M sodium hydroxide and then it was dried and evaporated. The product was recrystallized from toluene-heptane. extracted with diethyl ether The organic phase was washed with water and 5M sodium hydroxide it was dried evaporated The product was recrystallized from toluene-heptane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: After 6-hydroxy-2H-benzofuran-3-one 1 g and 3-ethoxy-4-benzyloxybenzaldehyde 1.80 g were dissolved in methanol 75 ml, concentrated hydrochloric acid 50 ml was added, and the mixture was refluxed for 1.5 hours. The solution was cooled to room temperature, and precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 1.33 g. the mixture was refluxed for 1.5 hours precipitated crystals were filtered dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure