4-prop-2-enoxybutanal

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13 mL of DMSO (246 mmol) was gradually added to a solution prepared by dissolving oxaryl chloride (5.8 mL, 66 mmol) in 123 mL of CHCl3, which solution had been cooled to −80° C., and the mixture was stirred for three minutes. 6.8 g of 4-allyloxy-1-butanol (52 mmol) was then added to the mixture. After the solution was stirred for 15 minutes, 43 mL of triethylamine (594 mmol) was added thereto and the reaction solution was stirred for 10 hours, while the temperature of the reaction solution was allowed to return to room temperature. The reaction was quenched by adding distilled water and the CHCl3 layer was separated. The separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine and dried with anhydrous Na2SO4. The solvent was distilled away under reduced pressure, whereby pale yellow liquid was obtained (6.0 g, 90%). prepared After the solution was stirred for 15 minutes the reaction solution was stirred for 10 hours, while the temperature of the reaction solution to return to room temperature The reaction was quenched by adding distilled water the CHCl3 layer was separated The separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine dried with anhydrous Na2SO4 The solvent was distilled away under reduced pressure, whereby pale yellow liquid was obtained (6.0 g, 90%)

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

Procedure: Conversion of formaldehyde was essentially complete. The crude product contained 4-propoxy-n-butyraldehyde and 4-allyloxy-n-butyraldehyde in a mol ratio of about 13:1, respectively.

Conditions: temp:-80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 13 mL of DMSO (246 mmol) was gradually added to a solution prepared by dissolving oxaryl chloride (5.8 mL, 66 mmol) in 123 mL of CHCl3, which solution had been cooled to −80° C., and the mixture was stirred for three minutes. 6.8 g of 4-allyloxy-1-butanol (52 mmol) was then added to the mixture. After the solution was stirred for 15 minutes, 43 mL of triethylamine (594 mmol) was added thereto and the reaction solution was stirred for 10 hours, while the temperature of the reaction solution was allowed to return to room temperature. The reaction was quenched by adding distilled water and the CHCl3 layer was separated. The separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine and dried with anhydrous Na2SO4. The solvent was distilled away under reduced pressure, whereby pale yellow liquid was obtained (6.0 g, 90%). prepared After the solution was stirred for 15 minutes the reaction solution was stirred for 10 hours, while the temperature of the reaction solution to return to room temperature The reaction was quenched by adding distilled water the CHCl3 layer was separated The separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine dried with anhydrous Na2SO4 The solvent was distilled away under reduced pressure, whereby pale yellow liquid was obtained (6.0 g, 90%)

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

Procedure: Conversion of formaldehyde was essentially complete. The crude product contained 4-propoxy-n-butyraldehyde and 4-allyloxy-n-butyraldehyde in a mol ratio of about 13:1, respectively.