8-Chloro-1-octene

6.99 g (purity 91.7percent; 0.05 mol) of 7-octen-1-ol, 5.93 g (0.075 mol) of pyridine, 5.93 g (0.075 mol) of pyridine, , And the temperature of the mixture inside was cooled to 5 ° C. with stirring. Then, 6.65 g (0.055 mol) of thionyl chloride was added dropwise over 0.5 hours while maintaining the internal temperature at 15 ° C. or lower. After completion of the dropwise addition, the mixture was heated to an internal temperature of 60 ° C. and heated and stirred for 10 hours. After cooling, 30 g of water was added and after stirring and standing, the aqueous phase was separated, and the organic phase was further washed with 30 g of 5percent sodium bicarbonate aqueous solution and then with 30 g of water. Analysis of the separated organic phase by gas chromatography revealed that 6.97 g (0.0475 mol; yield 95percent) of 7-octenyl chloride was formed. The reaction solution was purified by distillation to obtain 6.61 g (0.0451 mol; cumulative yield: 90percent) of 7-octenyl chloride.2.55 g (105 mmol) of metallic magnesium (20 to 50 mesh) and 75 g of tetrahydrofuran (THF) were charged in a 200 mL flask replaced with a nitrogen atmosphere, and the reaction solution was cooled to 0 ° C. with stirring. After cooling, 19.95 g (100 mmol) of 1-bromo-6-chlorohexane (solvent / dihaloalkane weight ratio 3.76) was added over about 2 hours and aged at the same temperature for 2 hours to obtain a Grignard reagent It was. Analysis of this reaction solution by gas chromatography (GC) revealed that the yield of the Grignard reagent was 86 areapercent and the selectivity was 86percent.In the case of0.16 g (1.0 mmol) of ferric chloride was added to the solution of the Grignard reagent obtained by the above operation, 6.25 g (100 mmol) of vinyl chloride was bubbled in over 2 hours while maintaining the temperature at 0 ° C., And aged at a temperature for 1 hour. After completion of the reaction, a 10percent ammonium chloride aqueous solution and methylene chloride were added, and the resultant salt was dissolved and separated. After fractionation of the organic layer, this was quantitatively analyzed by gas chromatography (GC). As a result, 8-chloro-1-octene as a target product was produced with a yield of 72percent. The results are shown in Table 4.

Molecular Weight:146.66
XLogP3:3.7
Rotatable Bond Count:6
Exact Mass:146.0862282
Monoisotopic Mass:146.0862282
Heavy Atom Count:9
Complexity:59.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes