[redballoons]

Devise a simple laboratory separation of the following compounds...

Anisole (bp. 158.3 °C)
Tripropylamine (bp. 156 °C)
Adipic acid (bp. 153 °C)



I was thinking you could treat the solution with NaHCO3 and separate aqueous and organic layers. The aqueous layer can then be treated with HCl to separate the Adipic acid. The organic layer can be treated with aqueous HCl and then the aqueous layer can be separated and treated with NaOH to give Tripropylamine. But I'm not sure how to separate anisole.

[Babcock_Hall]

Where would the anisole be after you treated with HCl?