HQDA → HCID 131717194, compound

Participants

Reaction Steps

The product was a light tan solid containing a large amount (~232.8 g) of excess, unreacted HQDA. Since HQDA solubility in methanol (CH3OH) is ~6.3 weight percent at 23° C., >4.7 liters of CH3OH should dissolve all unreacted HQDA. Therefore, the product was crushed into a fine powder and washed with 2.8 liters of methanol by slurrying the powder in the methanol for several hours and suction filtering through a 25-50μ frit. It was then treated similarly four more times, using 1.2 liters of methanol per trituration. Hence, the product was washed with a total of 7.6 liters of methanol, or 2.9 liters more than the amount required to dissolve 233 g. The solid product was dried and yielded 192 g (76.8 percent of theoretical) of HQDA/IPA/HQDA. The light tan solid melted at 140°-155° C. on a Fisher Johns hot stage melting point apparatus. The melting point determined by DSC was 156°-161° C. Proton NMR was run in DMSO. The spectrum is in good agreement with the expected bis-paraacetoxy ended aromatic ester.

Provenance & Evidence