4-hydroxy-3-propoxybenzaldehyde

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

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

Procedure: The preparation is carried out analogously to Example 2 from 0.76 g (4.22 mmol) of 4-hydroxy-3-propoxybenzaldehyde and 1.48 g (4.43 mmol) of methyl (triphenylphosphoranylidene)acrylate and gave 0.78 g of methyl (E)-4-hydroxy-3-propoxycinnamate.

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

Procedure: The preparation is carried out analogously to Example 2 from 0.76 g (4.22 mmol) of 4-hydroxy-3-propoxybenzaldehyde and 1.48 g (4.43 mmol) of methyl (triphenylphosphoranylidene)acrylate and gave 0.78 g of methyl (E)-4-hydroxy-3-propoxycinnamate.

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

Procedure: A mixture of 1.26 g (4.74 mmol) of 4-(5,5-dimethyl-1,3-dioxan-2-yl)-2-propoxyphenol, 20 ml of toluene and 20 ml of formic acid was vigorously stirred for 2 hours at room temperature. Thereafter, the reaction mixture was partitioned between toluene and water and the organic phase was washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Crystallization of the residue from a mixture of 10 ml of diethyl ether and 20 ml of hexane gave 0.78 mg of 4-hydroxy-3-propoxybenzaldehyde. Thereafter, the reaction mixture was partitioned between toluene and water the organic phase was washed several times with water dried over magnesium sulfate filtered evaporated down Crystallization of the residue from a mixture of 10 ml of diethyl ether and 20 ml of hexane

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

Procedure: 3,4-Dihydroxybenzaldehyde (0.5 g, 3.62 mmol) was dissolved in DMF (10 mL) and sodium hydride (0.087 g, 3.62 mmol) was added. The reaction mixture was stirred at rt for 10 min. Iodopropane (0.35 mL, 0.62 mmol) was added and the reaction was stirred at 80° C. for 2.5 h. The reaction was diluted with ethyl acetate and washed with 2N HCl and water. Silica gel chromatography eluting with 35% ethyl acetate/hexane yielded 0.16 g of desired product: ESI-MS 181 (M+H). the reaction was stirred at 80° C. for 2.5 h washed with 2N HCl and water Silica gel chromatography eluting with 35% ethyl acetate/hexane

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

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

Procedure: The preparation is carried out analogously to Example 2 from 0.76 g (4.22 mmol) of 4-hydroxy-3-propoxybenzaldehyde and 1.48 g (4.43 mmol) of methyl (triphenylphosphoranylidene)acrylate and gave 0.78 g of methyl (E)-4-hydroxy-3-propoxycinnamate.

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

Procedure: A mixture of 1.26 g (4.74 mmol) of 4-(5,5-dimethyl-1,3-dioxan-2-yl)-2-propoxyphenol, 20 ml of toluene and 20 ml of formic acid was vigorously stirred for 2 hours at room temperature. Thereafter, the reaction mixture was partitioned between toluene and water and the organic phase was washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Crystallization of the residue from a mixture of 10 ml of diethyl ether and 20 ml of hexane gave 0.78 mg of 4-hydroxy-3-propoxybenzaldehyde. Thereafter, the reaction mixture was partitioned between toluene and water the organic phase was washed several times with water dried over magnesium sulfate filtered evaporated down Crystallization of the residue from a mixture of 10 ml of diethyl ether and 20 ml of hexane

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

Procedure: 3,4-Dihydroxybenzaldehyde (0.5 g, 3.62 mmol) was dissolved in DMF (10 mL) and sodium hydride (0.087 g, 3.62 mmol) was added. The reaction mixture was stirred at rt for 10 min. Iodopropane (0.35 mL, 0.62 mmol) was added and the reaction was stirred at 80° C. for 2.5 h. The reaction was diluted with ethyl acetate and washed with 2N HCl and water. Silica gel chromatography eluting with 35% ethyl acetate/hexane yielded 0.16 g of desired product: ESI-MS 181 (M+H). the reaction was stirred at 80° C. for 2.5 h washed with 2N HCl and water Silica gel chromatography eluting with 35% ethyl acetate/hexane

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