5,7-dimethyladamantane-1,3-diol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.64 grams (10 millimoles) of 1,3-dimethyladamantane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 10 milliliters of acetic acid was stirred under oxygen atmosphere at a temperature of 70° C. for six hours. As a result, with a transformation rate for 1,3-dimethyladamantane of 99%, 1-hydroxy-3,5-dimethyladamantane (yield 39%), and 1,3-dihydroxy-5,7-dimethyladamantane (yield 58%) were obtained. The selectivity for the alcohols was 97%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction was conducted in the same manner as the step of Example 36 (2) except that 1,3-dimethyl-5,7-dihydroxyadamantane was used instead of the 1,3-dicarboxy-5-adamantanol, and, as a result, a 1,3-dimethyl-5-hydroxy-7-acryloyloxyadamantane (yield: 87%, white solid) was obtained.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-Dihydroxy-5,7-dimethyladamantane was synthesized in a similar manner as described for 1,3,5,7-tetrahydroadamantane. Into a 4-neck flask immersed in a cooling bath and equipped with a low-temperature condenser (-20° C.), an air-driven, well-sealed mechanical stirrer, a solid addition funnel, and a thermocouple, there were charged 4.5 grams, 1,3-dimethyladamantane (Aldrich, 99%+), 100 ml methylene chloride, 96 grams sodium bicarbonate, 100 ml double distilled water. Upon stirring and cooling the mixture to 0° C., 100 grams TFP were added and the temperature of the mixture went to 10° C. After the mixture was cooled down again to 0° C., 100 grams OXONE were added in the course of an hour. The reaction mixture was stirred at -5° C. for additional 20 hours (overnight). The TFP was recovered by distilling the reaction mixture at a pot temperature of 50° C. into a receiver immersed in DryIce/acetone. The remainder mixture was filtered by suction over Celite as a filter aid. The filtrate was yellow and contained two phases (aqueous and organic). It was rotavapped to dryness. The dry solid was extracted with ethanol and filtered. Crude product was obtained by evaporating off the ethanol which contained more than 95% 1,3-dihydroxy-5,7-dimethyladamantane. The brownish crude product was purified by crystallization from ethanol/methylene chloride mixture to a GC pure product with a molecular weight of 196 gram/mole (by GC-MS). Calculated for C12H20O2 :196.28 gram/mole Into a 4-neck flask immersed in a cooling bath equipped with a low-temperature condenser (-20° C.) an air-driven, well-sealed mechanical stirrer, a solid addition funnel 100 grams TFP were added went to 10° C After the mixture was cooled down again to 0° C. The reaction mixture was stirred at -5° C. for additional 20 hours (overnight) The TFP was recovered by distilling the reaction mixture at a pot temperature of 50° C. into a receiver The remainder mixture was filtered by suction over Celite as a filter aid The dry solid was extracted with ethanol filtered Crude product was obtained by evaporating off the ethanol which The brownish crude product was purified by crystallization from ethanol/methylene chloride mixture to a GC pure product with a molecular weight of 196 gram/mole (by GC-MS)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1.64 grams (10 millimoles) of 1,3-dimethyladamantane, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide, 0.015 gram (0.06 millimole) of Co(AA)2 and 10 milliliters of acetic acid was stirred under oxygen atmosphere at a temperature of 70° C. for six hours. As a result, with a transformation rate for 1,3-dimethyladamantane of 99%, 1-hydroxy-3,5-dimethyladamantane (yield 39%), and 1,3-dihydroxy-5,7-dimethyladamantane (yield 58%) were obtained. The selectivity for the alcohols was 97%.