isopropyl cyclopropanesulfonate Chemical Properties

storage temp. 

Sealed in dry,Store in freezer, under -20°C

Safety Information

HS Code 

2904100090

isopropyl cyclopropanesulfonate Usage And Synthesis

Synthesis

Isopropanol (11 L) was slowly added to pyridine (1850 g; 1890 mL) at 20 °C with continuous stirring for 1 hour. Subsequently, the reaction system was cooled to -10 °C to 2 °C and cyclopropanesulfonyl chloride (1100 g) was added dropwise. After the dropwise addition, the reaction was kept at this temperature with continued stirring for 70 hours. Consumption of cyclopropanesulfonyl chloride was confirmed to be 85% by NMR analysis. The reaction mixture was further cooled to 0 °C and an aqueous solution (600 mL) of sodium hydroxide (312 g) was added dropwise. Upon completion of the reaction, the mixture was concentrated to dryness at 45 °C. The concentrate was diluted with ethyl acetate (2750 mL) and methyl tert-butyl ether (1375 mL), stirred for 10 minutes and filtered. To the filtrate was added heptane (1375 mL), filtered again and the filtrate was concentrated to dryness to give 1080 g of isopropyl cyclopropyl sulfonate as a red liquid in 84% yield. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 4.86 (m, 1H), 2.83 (m, 1H), 1.33 (d, 6H), 0.98-1.10 (m, 4H).

References

[1] Patent: US2012/316149, 2012, A1. Location in patent: Page/Page column 13; 14
[2] Patent: WO2012/168884, 2012, A1. Location in patent: Page/Page column 33
[3] Patent: WO2010/145197, 2010, A1. Location in patent: Page/Page column 67-68
[4] Patent: EP3312172, 2018, A1. Location in patent: Paragraph 0399; 0400

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