2-hydroxy-6-methoxybenzaldehyde

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

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

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

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

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

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

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

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propyl bromide (1 ml) was added to a mixture of 2-hydroxy-6-methoxybenzaldehyde (0.45 g), potassium carbonate (0.83 g) and a small amount of potassium iodide in a mixed solvent of N,N-dimethylformamide (10 ml) and acetone (5 ml). After being stirred for 5 hours at 100° C., the mixture was poured into ice-water (20 ml) and extracted with ethyl acetate. The extract was washed with brine (10 ml), dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless oil of 2-methoxy-6-propoxybenzaldehyde (0.3 g). extracted with ethyl acetate The extract was washed with brine (10 ml) dried over magnesium sulfate evaporated under reduced pressure The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1) The fractions containing the objective compound were collected evaporated under reduced pressure

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

Procedure: The 3-(1-ethoxyethoxy)anisole was dissolved in ether (750 ml) and n-butyllithium (1.6M solution in hexanes; 500 ml) was added dropwise at ambient temperature under nitrogen. The mixture was stirred at ambient temperature for 2 hours, then it was cooled to 10° C. and a solution of dimethylformamide (94 g) in ether (150 ml) was added dropwise. The mixture was stirred at ambient temperature for 2 hours, then poured onto crushed ice. The product was extracted into ether, the combined extracts dried over magnesium sulphate, and the solvents removed in vacuo. The residual oil was dissolved in methanol (500 ml) and the stirred solution was cooled in ice and made strongly acidic by the addition of hydrochloric acid (2M). The resulting solid was collected by filtration, washed with water, dried in vacuo over phosphorus pentoxide and crystallised from petroleum ether (b.p. 60°-80° C.) to give 2-hydroxy-6-methoxybenzaldehyde as pale yellow needles (16 g), m.p. 69°-71° C. it was cooled to 10° C. The mixture was stirred at ambient temperature for 2 hours poured onto crushed ice The product was extracted into ether the combined extracts dried over magnesium sulphate the solvents removed in vacuo The residual oil was dissolved in methanol (500 ml) the stirred solution was cooled in ice made strongly acidic by the addition of hydrochloric acid (2M) The resulting solid was collected by filtration washed with water dried in vacuo over phosphorus pentoxide crystallised from petroleum ether (b.p. 60°-80° C.)

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

Procedure: 2-Hydroxy-6-methoxybenzaldehyde (4.56 g, 0.03 M), methyl 3-bromomethylbenzoate (6.87 g, 0.03 M), anhydrous potassium carbonate (4.455 g), sodium iodide (0.18 g) and methanol (50 ml) were refluxed with stirring for 18 hr. The cooled reaction mixture was filtered and the solid washed well with methanol. The filtrate was evaporated to dryness and the residue triturated with 1 N sodium hydroxide solution. The solid was filtered off and washed with water to give methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate, 3.27 g, 36%, m.p. 96°-97° C. from ethyl acetate/petrol. The cooled reaction mixture was filtered the solid washed well with methanol The filtrate was evaporated to dryness the residue triturated with 1 N sodium hydroxide solution The solid was filtered off washed with water