2,4-dihydroxy-5-methoxybenzaldehyde

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

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

Procedure: A mixture of 2,4-dihydroxy-5-methoxybenzaldehyde (1.68 g) and diethyl malonate (1.76 g) in DMF (5 ml) was treated with a few drops of piperidine and acetic acid and kept at 80-95° C. overnight. The reaction mixture was poured into ice water, acidified and filtered. Yield: 2.2. g. filtered

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

Procedure: A mixture of 2,4-dihydroxy-5-methoxybenzaldehyde (1.68 g) and diethyl malonate (1.76 g) in DMF (5 ml) was treated with a few drops of piperidine and acetic acid and kept at 80-95° C. overnight. The reaction mixture was poured into ice water, acidified and filtered. Yield: 2.2. g. filtered

Conditions: temp:22.01; 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: 2,4-Dihydroxy-5-methoxybenzaldehyde (6.0 g), benzyl bromide (9.7 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (8.6 g) in N,N-dimethylformamide (30 ml) were heated at 100° C. under nitrogen for 5 hours. After cooling to room temperature, 1 N NaOH was added and the mixture washed with ethyl acetate. The water phase was acidified with HCl and the precipitate was filtered. the mixture washed with ethyl acetate the precipitate was filtered

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

Procedure: 2,4,5-Trimethoxybenzaldehyde (20 g) was dissolved in dichloromethane (20 ml) and aluminum chloride (34.1 g) was added in small portions. The resulting mixture was stirred at room temperature for 5 hours and then poured in acidic ice water. The dichloromethane layer was separated and the water phase extracted with ethyl acetate. The combined organic layers were extracted with 1 N NaOH. The water phase was acidified with HCl and the precipitate was filtered. The product was recrystallized from toluene. The dichloromethane layer was separated the water phase extracted with ethyl acetate The combined organic layers were extracted with 1 N NaOH the precipitate was filtered The product was recrystallized from toluene

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

Procedure: A mixture of 2,4-dihydroxy-5-methoxybenzaldehyde (1.68 g) and diethyl malonate (1.76 g) in DMF (5 ml) was treated with a few drops of piperidine and acetic acid and kept at 80-95° C. overnight. The reaction mixture was poured into ice water, acidified and filtered. Yield: 2.2. g. filtered