1-chloro-4-(4-chlorobutoxy)butane

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

Procedure: 1-Methyl-2-nitroethyl-1'-acetylthiobutyl ether was prepared using procedures similar to those described in Examples I and II by chloroalkylation of 1-nitro-2-propanol with n-butyraldehyde and hydrogen chloride followed by treatment of the intermediate chlorobutyl ether with thiolacetic acid and then pyridine. Treatment of this nitroalkylacylthio ether in toluene with ethanolic sodium hydroxide as described in Example I afforded crude 4- oximino-2-propyl-5-methyl-1,3-oxathiolane comprised of a mixture of Isomer A (NMR data suggests Trans Isomer) and Isomer B (NMR suggests Cis). Trituration of 26 grams of the crude oxime mixture with 150 ml of hexane and filtration afforded 3.0 grams pure Isomer A, mp 86°-88°.

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

Procedure: 1-Methyl-2-nitroethyl-1'-acetylthiobutyl ether was prepared using procedures similar to those described in Examples I and II by chloroalkylation of 1-nitro-2-propanol with n-butyraldehyde and hydrogen chloride followed by treatment of the intermediate chlorobutyl ether with thiolacetic acid and then pyridine. Treatment of this nitroalkylacylthio ether in toluene with ethanolic sodium hydroxide as described in Example I afforded crude 4- oximino-2-propyl-5-methyl-1,3-oxathiolane comprised of a mixture of Isomer A (NMR data suggests Trans Isomer) and Isomer B (NMR suggests Cis). Trituration of 26 grams of the crude oxime mixture with 150 ml of hexane and filtration afforded 3.0 grams pure Isomer A, mp 86°-88°.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution comprising 14 g of allyl (4-chlorobutyl ether, 14 g of 4-hydroxybenzoic acid, 14 g of potassium carbonate and 50 ml of dimethylformamide was stirred at 90° C. for 3 hours. Water was added thereto, and the liquid was extracted with toluene. The toluene layer was washed well with water, and toluene was distilled off. Sodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue, and the solution was refluxed for 2 hours. Ethanol was distilled off, and hydrochloric acid was added to acidify the solution. It was extracted with diethyl ether and dried on anhydrous magnesium sulfate. The solvent was distilled off, and a residue thus obtained was recrystallized from a mixed solvent of ethanol and water to obtain 29 g of 4-(4-allyloxybutyloxy)benzoic acid. Phase transition temperature: C 94 N 107 I the liquid was extracted with toluene The toluene layer was washed well with water, and toluene was distilled off Sodium hydroxide 20 g, water 50 ml and ethanol 200 ml were added to the resulting residue the solution was refluxed for 2 hours Ethanol was distilled off hydrochloric acid was added It was extracted with diethyl ether dried on anhydrous magnesium sulfate The solvent was distilled off a residue thus obtained was recrystallized from a mixed solvent of ethanol and water

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

Procedure: 1-Methyl-2-nitroethyl-1'-acetylthiobutyl ether was prepared using procedures similar to those described in Examples I and II by chloroalkylation of 1-nitro-2-propanol with n-butyraldehyde and hydrogen chloride followed by treatment of the intermediate chlorobutyl ether with thiolacetic acid and then pyridine. Treatment of this nitroalkylacylthio ether in toluene with ethanolic sodium hydroxide as described in Example I afforded crude 4- oximino-2-propyl-5-methyl-1,3-oxathiolane comprised of a mixture of Isomer A (NMR data suggests Trans Isomer) and Isomer B (NMR suggests Cis). Trituration of 26 grams of the crude oxime mixture with 150 ml of hexane and filtration afforded 3.0 grams pure Isomer A, mp 86°-88°.