2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride

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

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: To a mixture containing 430 g of methanol and 265 g of pyridine, under ice cooled conditions, 501.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {wherein the molar ratio of the (1R)-trans compound: (1R)-cis compound: (1S)-trans compound: (1S)-cis compound was 93.9:2.5:3.5:0.1} was added over 2.5 hours while stirring the reaction mixture. Subsequently, the reaction mixture was further stirred at room temperature over 4 hours. After concentrating the reaction mixture under reduced pressure to about half of its volume, the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid. The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether and then concentrated to provide a residue. The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg) to provide 426 g of methyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. was added over 2.5 hours Subsequently, the reaction mixture was further stirred at room temperature over 4 hours After concentrating the reaction mixture under reduced pressure to about half of its volume the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether concentrated to provide a residue The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg)

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

Procedure: This compound was prepared in the manner of Example II using 3.3 g of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride, whose preparation is described in J. Sci. Food and Agriculture, 18, 325 (1967), 4.3 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour, then at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system to give as a residue 6.3 g of α-trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate. The ir spectrum was consistent with the assigned structure. This compound was prepared in the manner of Example II Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system

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

Procedure: This compound was prepared in the manner of Example II using 3.3 g of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride, whose preparation is described in J. Sci. Food and Agriculture, 18, 325 (1967), 4.3 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour, then at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system to give as a residue 6.3 g of α-trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate. The ir spectrum was consistent with the assigned structure. This compound was prepared in the manner of Example II Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system

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

Procedure: In 10 ml of tetrahydrofuran, 1.0 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl alcohol and 0.42 g of pyridine were dissolved, 0.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {stereoisomers ratio (1R)-trans:(1R)-cis:(1S)-trans:(1S)-cis=93.9:2.5:3.5:0.1} was added thereto and stirred for 8 hours at room temperature. After that, the reaction mixture was poured into about 50 ml of ice-water and extracted with 80 ml of ethyl acetate twice. The combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1.4 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropane-carboxylate. extracted with 80 ml of ethyl acetate twice The combined organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: In 10 ml of tetrahydrofuran, 1.0 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl alcohol and 0.42 g of pyridine were dissolved, 0.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {stereoisomers ratio (1R)-trans:(1R)-cis:(1S)-trans:(1S)-cis=93.9:2.5:3.5:0.1} was added thereto and stirred for 8 hours at room temperature. After that, the reaction mixture was poured into about 50 ml of ice-water and extracted with 80 ml of ethyl acetate twice. The combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1.4 g of 4-methoxymethy-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropane-carboxylate. extracted with 80 ml of ethyl acetate twice The combined organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: This compound was prepared in the manner of Example II using 3.3 g of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride, whose preparation is described in J. Sci. Food and Agriculture, 18, 325 (1967), 4.3 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour, then at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system to give as a residue 6.3 g of α-trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate. The ir spectrum was consistent with the assigned structure. This compound was prepared in the manner of Example II Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system

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

Procedure: This compound was prepared in the manner of Example II using 3.3 g of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarbonyl chloride, whose preparation is described in J. Sci. Food and Agriculture, 18, 325 (1967), 4.3 g of α-trifluoromethyl-3-phenoxybenzyl alcohol, and 1.5 g of pyridine in 50 ml of toluene. Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour, then at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system to give as a residue 6.3 g of α-trifluoromethyl-3-phenoxybenzyl 3-(2,2-dimethylvinyl)-2,2-dimethylcyclopropanecarboxylate. The ir spectrum was consistent with the assigned structure. This compound was prepared in the manner of Example II Volatiles were distilled from the crude reaction product at 90°/0.08 mm for 1/2 hour at 100°/0.08 mm for 3/4 hour through a short path Kugelrohr distillation system

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

Procedure: To a mixture containing 430 g of methanol and 265 g of pyridine, under ice cooled conditions, 501.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {wherein the molar ratio of the (1R)-trans compound: (1R)-cis compound: (1S)-trans compound: (1S)-cis compound was 93.9:2.5:3.5:0.1} was added over 2.5 hours while stirring the reaction mixture. Subsequently, the reaction mixture was further stirred at room temperature over 4 hours. After concentrating the reaction mixture under reduced pressure to about half of its volume, the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid. The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether and then concentrated to provide a residue. The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg) to provide 426 g of methyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. was added over 2.5 hours Subsequently, the reaction mixture was further stirred at room temperature over 4 hours After concentrating the reaction mixture under reduced pressure to about half of its volume the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether concentrated to provide a residue The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg)

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

Procedure: To a mixture containing 430 g of methanol and 265 g of pyridine, under ice cooled conditions, 501.9 g of 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic chloride {wherein the molar ratio of the (1R)-trans compound: (1R)-cis compound: (1S)-trans compound: (1S)-cis compound was 93.9:2.5:3.5:0.1} was added over 2.5 hours while stirring the reaction mixture. Subsequently, the reaction mixture was further stirred at room temperature over 4 hours. After concentrating the reaction mixture under reduced pressure to about half of its volume, the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid. The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether and then concentrated to provide a residue. The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg) to provide 426 g of methyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. was added over 2.5 hours Subsequently, the reaction mixture was further stirred at room temperature over 4 hours After concentrating the reaction mixture under reduced pressure to about half of its volume the reaction mixture was eye-dropped into 500 ml of 3.5% hydrochloric acid The resulting mixture was extracted 3 times with 200 ml of methyl-t-butyl ether concentrated to provide a residue The resulting residue was distilled under reduced pressure (84 to 89° C./7 mmHg)