tert-Butanol → HCID 41971, compound

Participants

Reaction Steps

The latter compound (5.4 g) was dissolved in 20 mL of 1:9 THF:tert-butanol and added dropwise to an ice cold solution of potassium tert-butoxide (6.75 g) in 100 mL of 1:9 THF:tert-butanol. The reaction mixture was stirred in ice for 1 hour and at room temperature for 0.5 hours. The reaction mixture was diluted with water (200 mL) and extracted with pentane (2×75 mL). The combined organic layer was washed with water (4×150 mL). The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to give an oil. Distillation gave 1.79 g (72% yield) of a 2:1 mixture of (Z)- and (E)-1,3-nonadiene as established by NMR, IR and capillary GC analysis.

Provenance & Evidence