2,2-diethoxyethyl benzoate

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: Chloroacetaldehyde diethyl acetal (1.9 g), potassium benzoate (2.0 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (60 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration and separation, the organic layer was concentrated and thereby yielded the target compound (0.69 g) in a yield of 30%. by refluxing After filtration and separation the organic layer was concentrated

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), benzoic acid (2.16 g), potassium iodide (0.27 g), potassium carbonate (1.11 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL;) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and thereby yielded the target compound (1.74 g) in a yield of 56%. by refluxing After filtration the organic layer was separated was subjected to vacuum concentration

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%. by refluxing After filtration the organic layer was washed with water (30 mL) was dried over anhydrous sodium sulfate Subsequent filtration and vacuum concentration

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%. by refluxing After filtration the organic layer was washed with water (30 mL) was dried over anhydrous sodium sulfate Subsequent filtration and vacuum concentration

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium iodide (0.41 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and then to Kugelrohr distillation at 110-120° C. and at 1 mmHg and thereby yielded the target compound (2.41 g) in a yield of 77%. by refluxing After filtration the organic layer was separated was subjected to vacuum concentration to Kugelrohr distillation at 110-120° C.

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

Procedure: To a pyridine (30 ml) solution of glycol aldehyde diethylacetal (19.8 g, 148 mmol), benzoyl chloride (51.7 ml, 444 mmol) was added dropwise at −20 to 30° C. The mixture was stirred at room temperature for 167 hours and 50 minutes. After methanol and water were added to the mixture, extraction with ethyl acetate was performed. The obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution, and a saturated saline solution. After dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and purified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9). Thereafter, purification by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10) was performed again to obtain the title compound (34 g, yield: 96.4%) as a light green oil. The obtained organic layer was washed with a saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogencarbonate solution After dried over anhydrous magnesium sulfate the mixture was concentrated under reduced pressure purified by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/9) Thereafter, purification by silica gel column chromatography (elution solvent: heptane, ethyl acetate/heptane=1/100, 1/30, 1/10)

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

Procedure: Chloroacetaldehyde diethyl acetal (1.9 g), potassium benzoate (2.0 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (60 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration and separation, the organic layer was concentrated and thereby yielded the target compound (0.69 g) in a yield of 30%. by refluxing After filtration and separation the organic layer was concentrated

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), benzoic acid (2.16 g), potassium iodide (0.27 g), potassium carbonate (1.11 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and thereby yielded the target compound (1.74 g) in a yield of 56%. by refluxing After filtration the organic layer was separated was subjected to vacuum concentration

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%. by refluxing After filtration the organic layer was washed with water (30 mL) was dried over anhydrous sodium sulfate Subsequent filtration and vacuum concentration

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

Procedure: Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium iodide (0.41 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and then to Kugelrohr distillation at 110-120° C. and at 1 mmHg and thereby yielded the target compound (2.41 g) in a yield of 77%. by refluxing After filtration the organic layer was separated was subjected to vacuum concentration to Kugelrohr distillation at 110-120° C.