4277-34-3

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.

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