Sodium Hydroxide → HCID 18695841, compound

Participants

Reaction Steps

4.5 g (118 mmol) of lithium aluminum hydride were added in portions to 9.4 g (38 mmol) of 4-p-fluorophenylcyclohex-1-ene-1,2-dicarboximide in 300 ml of tetrahydrofuran during the course of 45 min at room temperature and with good stirring. After stirring for 0.5 h, the mixture was refluxed for a further 6 h. After cooling, ten percent sodium hydroxide solution was carefully added dropwise with good stirring and with ice cooling and the precipitated hydroxides were filtered off with suction and washed with tetrahydrofuran. The filtrate was concentrated to dryness and the residue was partitioned between water and methyl t-butyl ether at pH=10. The organic phase was subsequently extracted twice with ten percent hydrochloric acid and the acidic aqueous phase was rendered alkaline again after this with concentrated sodium hydroxide solution. It was then extracted twice with methyl t-butyl ether. After drying and concentration, 1.8 g (22%) of product were isolated as a pale oil.

Provenance & Evidence