4-chloro-1,1-diethoxybutane

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

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

Procedure: A suspension of 1.44 g of sodium hydride in 100 ml of dimethylformamide is treated within 10 minutes with 9.75 g of 9-acridanone and held at 50° for 2 hours. At 120° there are then added 9.5 g of 4,4-diethoxybutyl chloride. After 16 hours, the mixture is cooled, poured into water and extracted with dichloromethane. The extract is dried over sodium sulfate and evaporated. The residue is extracted with hexane and crystallized twice from hexane. There is obtained 10-(4,4-diethoxybutyl)-9-acridanone of metling point 73°-74.5°. After 16 hours the mixture is cooled extracted with dichloromethane The extract is dried over sodium sulfate evaporated The residue is extracted with hexane crystallized twice from hexane

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

Procedure: A suspension of 1.44 g of sodium hydride in 100 ml of dimethylformamide is treated within 10 minutes with 9.75 g of 9-acridanone and held at 50° for 2 hours. At 120° there are then added 9.5 g of 4,4-diethoxybutyl chloride. After 16 hours, the mixture is cooled, poured into water and extracted with dichloromethane. The extract is dried over sodium sulfate and evaporated. The residue is extracted with hexane and crystallized twice from hexane. There is obtained 10-(4,4-diethoxybutyl)-9-acridanone of metling point 73°-74.5°. After 16 hours the mixture is cooled extracted with dichloromethane The extract is dried over sodium sulfate evaporated The residue is extracted with hexane crystallized twice from hexane

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

Procedure: A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg). Yield 5.5 g. the reaction mixture is added to 600 ml distilled water The product is extracted with dichloromethane (150, 125, and 125 ml) The combined extracts are then dried with anhydrous magnesium sulfate the solvent is distilled off under reduced pressure Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg)

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

Procedure: A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg). Yield 5.5 g. the reaction mixture is added to 600 ml distilled water The product is extracted with dichloromethane (150, 125, and 125 ml) The combined extracts are then dried with anhydrous magnesium sulfate the solvent is distilled off under reduced pressure Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg)

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

Procedure: A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg). Yield 5.5 g. NMR (d6-DMSO): 1.11 ppm (t, 6H), 1.53 ppm (m, —CH2CH, 2H), 1.64 ppm (m, —CH2CH2CH, 2H), 3.37 ppm (t, —O—CH9CH2CH2CH, 2H), 3.53 ppm (t, HO—CH2CH2O—, 2H), 3.62 ppm (q, —CH2CH3, 4H), 3.70 ppm (t, HO—CH2—, 2H), 4.38 ppm (t, —CH acetal, 1H), 4.54 ppm (t, 1H, —OH). the reaction mixture is added to 600 ml distilled water The product is extracted with dichloromethane (150, 125, and 125 ml) The combined extracts are then dried with anhydrous magnesium sulfate the solvent is distilled off under reduced pressure Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg)

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

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

Procedure: Salicylhydroxamic acid (30 g.) and 36 g. of 4-chlorobutyraldehyde diethyl acetal were allowed to react in acetic acid as described in Example 1. The reaction mixture was transferred to an ice-water mixture, stirred well, and decanted to remove the aqueous layer. The oil was washed again with water and allowed to stand at room temperature whereupon crystallization occurred. Aqueous solution of ammonium hydroxide was added, mixture was warmed and stirred and then allowed to stand overnight at room temperature. The aqueous solution was decanted from the partially crystallized oil and the latter was triturated with ethanol yielding 9.5 g. of solid melting at 137.5°-139.5° C. After recrystallization from methanol, the product (7 g.) melted at 139°-141° C. decanted to remove the aqueous layer The oil was washed again with water to stand at room temperature whereupon crystallization Aqueous solution of ammonium hydroxide was added mixture was warmed stirred The aqueous solution was decanted from the partially crystallized oil the latter was triturated with ethanol yielding 9.5 g After recrystallization from methanol

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

Procedure: Salicylhydroxamic acid (30 g.) and 36 g. of 4-chlorobutyraldehyde diethyl acetal were allowed to react in acetic acid as described in Example 1. The reaction mixture was transferred to an ice-water mixture, stirred well, and decanted to remove the aqueous layer. The oil was washed again with water and allowed to stand at room temperature whereupon crystallization occurred. Aqueous solution of ammonium hydroxide was added, mixture was warmed and stirred and then allowed to stand overnight at room temperature. The aqueous solution was decanted from the partially crystallized oil and the latter was triturated with ethanol yielding 9.5 g. of solid melting at 137.5°-139.5° C. After recrystallization from methanol, the product (7 g.) melted at 139°-141° C. decanted to remove the aqueous layer The oil was washed again with water to stand at room temperature whereupon crystallization Aqueous solution of ammonium hydroxide was added mixture was warmed stirred The aqueous solution was decanted from the partially crystallized oil the latter was triturated with ethanol yielding 9.5 g After recrystallization from methanol

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

Procedure: 6-Chloro-2-(3-chloropropyl)-2,3-dihydro-3-hydroxy-4H-1,3-benzoxazin-4-one was prepared by adding 250 ml. of glacial acetic acid saturated with hydrogen chloride gas to 37 g. of 5-chlorosalicylhydroxamic acid. 4-Chlorobutyraldehyde diethyl acetal (34 g.) and 50 ml. of glacial acetic acid saturated with hydrogen chloride gas were then added simultaneously with stirring at a rate to maintain a temperature of 25° to 40° C. The resulting mixture was stirred and heated at 55° to 60° C. for 2 hours and then allowed to stand at room temperature overnight. Mixture was poured into a mixture of ice and water, and when oil solidified it was removed by filtrating, washed with water, and air-dried. The crude product weighed 31.5 g. and melted at 70°-75° C. A sample recrystallized from ligroin at 80°-81° C. by adding 250 ml to maintain a temperature of 25° to 40° C The resulting mixture was stirred heated at 55° to 60° C. for 2 hours was removed by filtrating washed with water air-dried A sample recrystallized from ligroin at 80°-81° C.

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

Procedure: A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg). the reaction mixture is added to 600 ml distilled water The product is extracted with dichloromethane (150, 125, and 125 ml) The combined extracts are then dried with anhydrous magnesium sulfate the solvent is distilled off under reduced pressure Next the product is subjected to vacuum distillation (kugelrohr, t=90-110° C., 0.10 mm Hg)

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

Procedure: A mixture of anhydrous ethylene glycol (120 g, 1.93 moles), a 1.0M solution of potassium tert-butoxide in tert-butanol (70 ml, 0.07 moles), and 4-chlorobutyraldehyde diethyl acetal (11 g, 0.061 moles) is stirred overnight at 100° C. under an argon atmosphere. After cooling to room temperature, the reaction mixture is added to 600 ml distilled water. The product is extracted with dichloromethane (150, 125, and 125 ml). The combined extracts are then dried with anhydrous magnesium sulfate and the solvent is distilled off under reduced pressure. Next the product is subjected to vacuum distillation (kugelrohr, t=90–110° C., 0.10 mm Hg). Yield 5.5 g. the reaction mixture is added to 600 ml distilled water The product is extracted with dichloromethane (150, 125, and 125 ml) The combined extracts are then dried with anhydrous magnesium sulfate the solvent is distilled off under reduced pressure Next the product is subjected to vacuum distillation (kugelrohr, t=90–110° C., 0.10 mm Hg)