5-carbomethoxy-6-hydroxysalicylaldehyde

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

Procedure: Methyl 2,4-dihydroxy-3-formylbenzoate (10.0 g, 0.051 M) was added to dimethylformamide (100 ml), then to this mixture was added sodium hydride (1.344 g, 0.056 M), portionwise. The mixture became warm and effervescence occurred. When the addition was complete the reaction mixture was left to stir at room temperature for 10 minutes. To this solution was then added sodium iodide (0.765 g), ethyl 5-bromovalerate (11.7 g, 0.056 M), and a further 20 ml of dimethylformamide. The whole was brought to 60° C. and left to stir for 5 days. The reaction mixture was cooled, poured into water (200 ml), acidified with concentrated hydrochloric acid, and extracted into ethyl acetate (2×75 ml). The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml), dried (magnesium sulphate), filtered and the solvent removed in vacuo to give ethyl 5-(2-formyl-3-hydroxy-4-methoxycarbonylphenoxy)pentanoate 6.92 g, 42% as a yellow oil, purified by column chromatography and obtained as a pale-yellow solid. The mixture became warm When the addition was left was brought to 60° C. left to stir for 5 days The reaction mixture was cooled extracted into ethyl acetate (2×75 ml) The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml) dried (magnesium sulphate) filtered the solvent removed in vacuo

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

Procedure: Methyl 2,4-dihydroxy-3-formylbenzoate (10.0 g, 0.051 M) was added to dimethylformamide (100 ml), then to this mixture was added sodium hydride (1.344 g, 0.056 M), portionwise. The mixture became warm and effervescence occurred. When the addition was complete the reaction mixture was left to stir at room temperature for 10 minutes. To this solution was then added sodium iodide (0.765 g), ethyl 5-bromovalerate (11.7 g, 0.056 M), and a further 20 ml of dimethylformamide. The whole was brought to 60° C. and left to stir for 5 days. The reaction mixture was cooled, poured into water (200 ml), acidified with concentrated hydrochloric acid, and extracted into ethyl acetate (2×75 ml). The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml), dried (magnesium sulphate), filtered and the solvent removed in vacuo to give ethyl 5-(2-formyl-3-hydroxy-4-methoxycarbonylphenoxy)pentanoate 6.92 g, 42% as a yellow oil, purified by column chromatography and obtained as a pale-yellow solid. The mixture became warm When the addition was left was brought to 60° C. left to stir for 5 days The reaction mixture was cooled extracted into ethyl acetate (2×75 ml) The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml) dried (magnesium sulphate) filtered the solvent removed in vacuo

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

Procedure: Methyl 2,4-dihydroxy-3-formylbenzoate (10.0 g, 0.051 M) was added to dimethylformamide (100 ml), then to this mixture was added sodium hydride (1.344 g, 0.056 M), portionwise. The mixture became warm and effervescence occurred. When the addition was complete the reaction mixture was left to stir at room temperature for 10 minutes. To this solution was then added sodium iodide (0.765 g), ethyl 5-bromovalerate (11.7 g, 0.056 M), and a further 20 ml of dimethylformamide. The whole was brought to 60° C. and left to stir for 5 days. The reaction mixture was cooled, poured into water (200 ml), acidified with concentrated hydrochloric acid, and extracted into ethyl acetate (2×75 ml). The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml), dried (magnesium sulphate), filtered and the solvent removed in vacuo to give ethyl 5-(2-formyl-3-hydroxy-4-methoxycarbonylphenoxy)pentanoate 6.92 g, 42% as a yellow oil, purified by column chromatography and obtained as a pale-yellow solid. The mixture became warm When the addition was left was brought to 60° C. left to stir for 5 days The reaction mixture was cooled extracted into ethyl acetate (2×75 ml) The combined organic layers were washed with water (2×75 ml), 5% sodium hydroxide solution (50 ml), water (50 ml) and brine (50 ml) dried (magnesium sulphate) filtered the solvent removed in vacuo