4-(3-methylbutoxy)benzaldehyde

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

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

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

Procedure: Lithium aluminum hydride (350 mg) was added gradually to a solution of 1.35 g of p-(3-methylbutoxy)-benzaldehyde in 50 ml of tetrahydrofuran at -10° C. After stirring at room temperature for 1 hour, the excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off from the mixture, and the filtrate was concentrated to give 1.33 g of p-(3-methylbutoxy)benzyl alcohol. Thionyl chloride (3 g) was added to a solution of the compound obtained in 25 ml of benzene, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to give 1.45 g of p-(3-methylbutoxy)benzyl chloride. To a solution of this compound in 50 ml of N,N-dimethylformamide, there was added a solution of 3.3 g of sodium azide in 14 ml of water with ice cooling. After overnight stirring at room temperature, the reaction mixture was diluted with water, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.48 g of p-(3-methylbutoxy)benzyl azide. To a solution of this compound in 30 ml of tetrahydrofuran was added 500 mg of lithium aluminum hydride with ice cooling. The temperature of the reaction mixture was allowed to gradually rise to room temperature, and the mixture was stirred for 2 hours. The excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to give 1.13 g of p-(3-methylbutoxy)benzylamine. The insoluble matter was filtered off from the mixture the filtrate was concentrated

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

Procedure: Lithium aluminum hydride (350 mg) was added gradually to a solution of 1.35 g of p-(3-methylbutoxy)-benzaldehyde in 50 ml of tetrahydrofuran at -10° C. After stirring at room temperature for 1 hour, the excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off from the mixture, and the filtrate was concentrated to give 1.33 g of p-(3-methylbutoxy)benzyl alcohol. Thionyl chloride (3 g) was added to a solution of the compound obtained in 25 ml of benzene, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to give 1.45 g of p-(3-methylbutoxy)benzyl chloride. To a solution of this compound in 50 ml of N,N-dimethylformamide, there was added a solution of 3.3 g of sodium azide in 14 ml of water with ice cooling. After overnight stirring at room temperature, the reaction mixture was diluted with water, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.48 g of p-(3-methylbutoxy)benzyl azide. To a solution of this compound in 30 ml of tetrahydrofuran was added 500 mg of lithium aluminum hydride with ice cooling. The temperature of the reaction mixture was allowed to gradually rise to room temperature, and the mixture was stirred for 2 hours. The excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to give 1.13 g of p-(3-methylbutoxy)benzylamine. The insoluble matter was filtered off from the mixture the filtrate was concentrated

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

Procedure: A mixture of 1.00 g of p-hydroxybenzaldehyde, 1.46 g of isoamyl iodide and 1.80 g of potassium carbonate in 15 ml of N,N-dimethylformamide was stirred at room temperature for 2 days. Water was added to the reaction mixture, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed in sequence with 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.34 g of p-(3-methylbutoxy)benzaldehyde. the product was extracted with ethyl acetate The ethyl acetate layer was washed in sequence with 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: The compound was synthesized as in Example 24.1, using 4-hydroxybenzaldehyde (200 mg, 1.64 mmol) and 1-iodo-3-methylbutane (649 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 4-(isopentyloxy)benzaldehyde (292 mg, quant. crude) as a dark yellow oil that was used without further purification or characterization. The compound was synthesized as in Example 24.1

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

Procedure: The compound was synthesized as in Example 24.1, using 4-hydroxybenzaldehyde (200 mg, 1.64 mmol) and 1-iodo-3-methylbutane (649 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 4-(isopentyloxy)benzaldehyde (292 mg, quant. crude) as a dark yellow oil that was used without further purification or characterization. The compound was synthesized as in Example 24.1

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

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

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

Procedure: Lithium aluminum hydride (350 mg) was added gradually to a solution of 1.35 g of p-(3-methylbutoxy)-benzaldehyde in 50 ml of tetrahydrofuran at -10° C. After stirring at room temperature for 1 hour, the excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off from the mixture, and the filtrate was concentrated to give 1.33 g of p-(3-methylbutoxy)benzyl alcohol. Thionyl chloride (3 g) was added to a solution of the compound obtained in 25 ml of benzene, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to give 1.45 g of p-(3-methylbutoxy)benzyl chloride. To a solution of this compound in 50 ml of N,N-dimethylformamide, there was added a solution of 3.3 g of sodium azide in 14 ml of water with ice cooling. After overnight stirring at room temperature, the reaction mixture was diluted with water, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.48 g of p-(3-methylbutoxy)benzyl azide. To a solution of this compound in 30 ml of tetrahydrofuran was added 500 mg of lithium aluminum hydride with ice cooling. The temperature of the reaction mixture was allowed to gradually rise to room temperature, and the mixture was stirred for 2 hours. The excess lithium aluminum hydride was decomposed with sodium sulfate decahydrate. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to give 1.13 g of p-(3-methylbutoxy)benzylamine. The insoluble matter was filtered off from the mixture the filtrate was concentrated

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

Procedure: A mixture of 1.00 g of p-hydroxybenzaldehyde, 1.46 g of isoamyl iodide and 1.80 g of potassium carbonate in 15 ml of N,N-dimethylformamide was stirred at room temperature for 2 days. Water was added to the reaction mixture, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed in sequence with 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.34 g of p-(3-methylbutoxy)benzaldehyde. the product was extracted with ethyl acetate The ethyl acetate layer was washed in sequence with 1N sodium hydroxide, water and saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure

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

Procedure: The compound was synthesized as in Example 24.1, using 4-hydroxybenzaldehyde (200 mg, 1.64 mmol) and 1-iodo-3-methylbutane (649 mg, 1.97 mmol) in place of 1-chloro-3,3-dimethylbutane (no sodium iodide was used) to give 4-(isopentyloxy)benzaldehyde (292 mg, quant. crude) as a dark yellow oil that was used without further purification or characterization. The compound was synthesized as in Example 24.1