3-bromo-4-prop-2-enoxybenzaldehyde

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

Procedure: 3-Bromo-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.083 mol) was heated under reflux in 75 ml mesitylene (1,3,5-trimethylbenzene) for 20 hours. After cooling, 250 ml 2N sodium hydroxide were added to the reaction mixture. The aqueous phase was washed two times with diethyl ether. The aqueous phase was subsequently acidified with concentrated hydrochloric acid under ice cooling and then extracted with ethyl acetate. After drying and concentrating the organic phase, there remained an oil that crystallized on cooling. After cooling The aqueous phase was washed two times with diethyl ether extracted with ethyl acetate After drying concentrating the organic phase crystallized on cooling

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

Procedure: 3-Bromo-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.083 mol) was heated under reflux in 75 ml mesitylene (1,3,5-trimethylbenzene) for 20 hours. After cooling, 250 ml 2N sodium hydroxide were added to the reaction mixture. The aqueous phase was washed two times with diethyl ether. The aqueous phase was subsequently acidified with concentrated hydrochloric acid under ice cooling and then extracted with ethyl acetate. After drying and concentrating the organic phase, there remained an oil that crystallized on cooling. After cooling The aqueous phase was washed two times with diethyl ether extracted with ethyl acetate After drying concentrating the organic phase crystallized on cooling

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

Procedure: 3-Bromo-4-hydroxybenzaldehyde (20.1 g, 0.100 mol) and allyl bromide (14.5 g, 0.120 mol) were heated under reflux together with potassium carbonate (20.7 g, 0.150 mol) in 150 ml acetone (abs.) for 8 hours. After cooling, the solid was filtered off and washed with acetone. After complete concentration of the organic phase, there was obtained an oily residue that was used directly in the second step without further purification. After cooling the solid was filtered off washed with acetone After complete concentration of the organic phase there was obtained an oily residue that was used directly in the second step without further purification

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

Procedure: 3-Bromo-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.083 mol) was heated under reflux in 75 ml mesitylene (1,3,5-trimethylbenzene) for 20 hours. After cooling, 250 ml 2N sodium hydroxide were added to the reaction mixture. The aqueous phase was washed two times with diethyl ether. The aqueous phase was subsequently acidified with concentrated hydrochloric acid under ice cooling and then extracted with ethyl acetate. After drying and concentrating the organic phase, there remained an oil that crystallized on cooling. After cooling The aqueous phase was washed two times with diethyl ether extracted with ethyl acetate After drying concentrating the organic phase crystallized on cooling

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

Procedure: 3-Bromo-4-hydroxybenzaldehyde (20.1 g, 0.100 mol) and allyl bromide (14.5 g, 0.120 mol) were heated under reflux together with potassium carbonate (20.7 g, 0.150 mol) in 150 ml acetone (abs.) for 8 hours. After cooling, the solid was filtered off and washed with acetone. After complete concentration of the organic phase, there was obtained an oily residue that was used directly in the second step without further purification. After cooling the solid was filtered off washed with acetone After complete concentration of the organic phase there was obtained an oily residue that was used directly in the second step without further purification