I have the following question for homework and am stumped. I am tasked with separating 3-(2-methoxyphenoxy)propane-1,2-diol and (1​*R*,2​*S*)-2-(methylamino)-1-phenylpropan-1-ol. They are both solvated in water.

![compounds](https://i.imgur.com/YsLM0up.png)

I was thinking to work up with acid to cleave the ethers on the left compound, but that won't do much to reduce solubility for crystallization. Esterification with a large hydrophobic carboxylic acid wouldn't do much either because both compounds have hydroxyls. Anyone have suggestions?