Synthesis
To a reaction flask equipped with a stirrer was added (z)-3,7-dimethyl-2,6-octadien-1-ol (nerolidol) (2) 5.7 mL (32.5 mmol), 28 mL of acetonitrile, 8 mL of buffer at pH=7, 2,2,6,6-tetramethylpiperidine oxide (TEMPO) 490 mg (3.24 mmol), and iodobenzene dichloroacetate 11.49 g (35.71 mmol). The reaction was stirred at 0C until TLC detection no longer showed raw material absorption spots of nerolidol (the reaction proceeded rapidly, and the reaction was essentially over in about 20 min). 100 mL of ether was added, transferred to a separatory funnel and washed twice with sodium thiosulfate solution. Separate the organic layer, the aqueous layer was extracted with ether 3 times. Combine the organic layers and wash sequentially with saturated sodium bicarbonate and saturated brine. Anhydrous sodium sulfate was dried, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by passing through silica gel column, eluted with ether-hexane (1:9), and finally (Z)-3,7-dimethyl-2,6-octadienal was obtained.
