Dichloromethane → 5,7-Dimethyladamantane-1,3-diol

温度

0 °C

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

1. customInto a 4-neck flask immersed in a cooling bath
2. customequipped with a low-temperature condenser (-20° C.)
3. customan air-driven, well-sealed mechanical
4. additionstirrer, a solid addition funnel
5. addition100 grams TFP were added
6. customwent to 10° C
7. temperatureAfter the mixture was cooled down again to 0° C.
8. stirringThe reaction mixture was stirred at -5° C. for additional 20 hours (overnight)
9. customThe TFP was recovered
10. distillationby distilling the reaction mixture at a pot temperature of 50° C. into a receiver
11. filtrationThe remainder mixture was filtered by suction over Celite as a filter aid
12. extractionThe dry solid was extracted with ethanol
13. filtrationfiltered
14. customCrude product was obtained
15. customby evaporating off the ethanol which
16. customThe 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)

ORDレコード

ord-f98ca2cc631141e6b91dd11c06408f43

出典データセット

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05576355