[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:16]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:17][CH2:18][C:19]([CH3:21])=O.C(=O)(O)[O-].[Na+]>O.C1(C)C=CC=CC=1>[CH2:1]1[O:4][C:19]([CH3:21])([CH2:18][CH2:17][C:16]([O:23][CH2:24][CH3:25])=[O:22])[O:3][CH2:2]1A mixture of about 110.86 g of ethylene glycol, about 2 g of p-toluenesulfonic acid and about 800 ml of toluene was refluxed using a Dean-Stark trap until no more water came off. An about 250 g portion of ethyl levulinate was added and refluxing was continued until no more water came off. The mixture was then cooled to room temperature, poured into saturated sodium bicarbonate, the organic layer dried and the solvent removed. The residue was distilled (about 67°-70° C., 0.35 mm) and the distillate stirred for about 20 minutes with about 6 g of sodium borohydride in ethanol. The solvent was removed, the residue dissolved in ether, washed with saturated sodium bicarbonate, dried and then distilled (about 41°-45° C., 0.3 mm), giving about 83 g of the desired title compound.
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