3-butoxy-4-hydroxybenzaldehyde

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

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

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.3 g (188 mmol) of sodium is put at the bottom of a flask under nitrogen and 40 ml of 1-butanol is poured on top. The reaction mixture is stirred and heated progressively up to 120° C.; as the butanolate formed is sparingly soluble, 20 ml of 1-butanol is added. When all the sodium has been consumed, the reaction mixture is brought back to room temperature and 40 ml of dimethylformamide is added. Under nitrogen, 6.8 g (68.2 mmol) of copper(I) chloride is added and then 12.4 g (62 mmol) of 3-bromo-4-hydroxy-benzaldehyde. The reaction mixture is heated progressively to 120° C. and stirred for 2 hours. After cooling to room temperature and then acidifying to pH5 with aqueous hydrochloric acid of concentration 2M, the reaction mixture is extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. After trituration and then recrystallization of the residue from pentane, 9.7 g (81%) of 3-butoxy-4-hydroxy-benzaldehyde is obtained. When all the sodium has been consumed is brought back to room temperature 40 ml of dimethylformamide is added After cooling to room temperature the reaction mixture is extracted with ethyl acetate washed with saturated sodium chloride solution dried over magnesium sulfate filtered evaporated After trituration and then recrystallization of the residue from pentane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.0 g (20.6 mmol) of 3-butoxy-4-hydroxybenzaldehyde and 13.25 g (30.9 mmol) of (methoxy(methoxycarbonyl)methyl)triphenylphosphonium chloride are suspended in 40 ml of tetrahydrofuran. 6 ml (42 mmol) of triethylamine are added and then the reaction medium is stirred at 40° C. for 16 hours. The reaction medium is filtered and then the solvents are evaporated. 50 ml of diethyl ether are added and the mixture is stirred at ambient temperature for 10 minutes and then filtered. After evaporation of the solvents, the residue is taken up in a heptane/ethyl acetate 8/2 mixture and then filtered through a silica patch (2 cm). 5.3 g of methyl (Z)-3-(3-butoxy-4-hydroxyphenyl)-2-methoxyacrylate are obtained after evaporation of the solvents. The reaction medium is filtered the solvents are evaporated 50 ml of diethyl ether are added the mixture is stirred at ambient temperature for 10 minutes filtered After evaporation of the solvents filtered through a silica patch (2 cm)

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

Procedure: 2.16 g (93.9 mmol) of sodium are dissolved in 15 ml of n-butanol at 110° C. for 3 hours. 20 ml of dimethylformamide are added at ambient temperature and then the medium is degassed several times. 3.4 g (34.1 mmol) of copper(I) chloride are added at ambient temperature and then the reaction medium is stirred for 10 minutes. 6.2 g (31 mmol) of 3-bromo-4-hydroxybenzaldehyde are added and then the reaction medium is stirred at 120° C. for 2 hours. The reaction mixture is cooled to ambient temperature and then the reaction is halted by the addition of 50 ml of a 2M hydrochloric acid solution. The medium is extracted with 250 ml of ethyl acetate. The solvents are evaporated and then the residue is filtered through a silica gel patch (2 cm): eluent heptane/ethyl acetate 8/2. After evaporation of the solvents, 5.55 g of orange oil are obtained. This oil is crystallized from pentane. 4.8 g of 3-butoxy-4-hydroxybenzaldehyde are obtained in the form of a brown solid after filtration. the medium is degassed several times the reaction medium is stirred at 120° C. for 2 hours The medium is extracted with 250 ml of ethyl acetate The solvents are evaporated the residue is filtered through a silica gel patch (2 cm) After evaporation of the solvents, 5.55 g of orange oil are obtained This oil is crystallized from pentane