cyclooct-4-en-1-ol

Synthesis

The general procedure for the synthesis of 4-hydroxycyclooctene from 5,6-epoxycyclooctene was as follows: 1. Preparation of (Z)-epoxy-4-enol (1): 9-oxabicyclo[6.1.0]non-4-ene (4.2 g, 33.8 mmol) was slowly added to LiAlH4 (1.2 g, 30.4 mmol) suspended in ether (100 mL). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, 4 mL of H2O, 4 mL of 25% NaOH (aq) and 4 mL of H2O were added sequentially for post-treatment. The resulting mixture was filtered and the filtrate was dried with Na2SO4 and filtered again. Concentration of the clarified ether solution gave 4.1 g (Z)-cyclooct-4-enol in 96.1% yield.

References

[1] Patent: US2013/309170, 2013, A1. Location in patent: Paragraph 0154
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 38, p. 10242 - 10246
[3] Angew. Chem., 2014, vol. 126, # 38, p. 10407 - 10412,5
[4] Patent: US2016/115180, 2016, A1. Location in patent: Paragraph 0139
[5] Macromolecules, 2005, vol. 38, # 25, p. 10406 - 10412