C(=O)/C=C/C1C=CC=CC=1.[OH:11][CH2:12][CH:13]([CH2:15][OH:16])[OH:14].C1(CCC[CH2:26][CH:27]([OH:30])[CH2:28][OH:29])C=CC=CC=1.C1(CCCCC(O)CO)CCCCC1>[Pd]>[CH2:12]([O:11][CH2:26][CH:27]([CH2:28][OH:29])[OH:30])[CH:13]([CH2:15][OH:16])[OH:14]Trans-Cinnamaldehyde (13.2 g, 12.6 ml, 0.1 mol) of, glycerol (92.09 g, 73.7 ml, 1 mol) and 10% Pd/C (0.66 g, 5 wt % relative to the aldehyde) are charged to a Parr reactor, purged three times with nitrogen, heated to 200° C. with stirring and reacted at 1000 psi of hydrogen for 20 h. GC analysis shows complete consumption of the aldehyde. The mixture is filtered, the product extracted with ether (50 ml×5), and the combined ether solution is dried with sodium sulfate. The solvent is evaporated and the residue chromatographed on silica gel using hexane-ethyl acetate from 5:1 to 1:1 to give 4.6 g of the monoether (95% purity). This product is approximately a 2:1 mixture of 3-(3-phenylpropyl)-1,2-propanediol and 3-(3-cyclohexylpropyl)-1,2-propanediol. The individual components of this mixture are separated by second column chromatography and characterized by 1H and 13C NMR.
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