65253-04-5

CLEAR COLOURLESS OILY LIQUID

(-)-8-Phenylmenthol is used to prepare piperidine-based analogs of cocaine as monoamine reuptake inhibitors. It is also used to prepare quinuclidinyl (fluoroalkyl)benzilate as muscarinic receptor antagonist.

Dissolve the menthol in toluene, dry (Na2SO4), evaporate and chromatograph it on a silica gel column and eluting with 5% Et2O in pet ether to give an oil with the desired rotation. IR has max 3420cm-1 (OH) with consistent 1H NMR [Corey & Ensley J Org Chem 43 1610 1978, Whitesell et al. Tetrahedron 42 2993 1986, Bednarski & Danishefsky J Am Chem Soc 108 7060 1986].