Reaction #57409

Reaction equation

α-bromotricyclo[3.3.1.13,7]decane-1-acetic acid

α-bromotricyclo[3.3.1.13,7]decane-1-acetic acid

H2SO4

HNO3

→

α-bromo-3-hydroxytricyclo [3.3.1.13,7]decane-1-acetic acid

Solvents

Water

Conditions

Workup

1. 1
   TemperatureThe flask is then cooled in an ice bath
2. 2
   TemperatureThe reaction is then heated to 60° C.
3. 3
   Otheris obtained
4. 4
   Temperatureit is cooled to and
5. 5
   Temperaturemaintained at room temperature
6. 6
   Otherto quench
7. 7
   Otherthe reaction
8. 8
   TemperatureThe resulting slurry is cooled in an ice bath
9. 9
   Filtrationfiltered

Procedure

α-Bromotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula O) is then reacted with H2SO4 and HNO3 to produce α-bromo-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula Q). More specifically, α-bromo-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (Formula Q) is prepared from α-bromotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula O) by first charging an Erlen-Meyer flask with H2SO4. The flask is then cooled in an ice bath and 50% HNO3 is added to the flask. The solid α-bromotricyclo[3.3.1.13,7]decane-1-acetic acid (Formula O) is then added to the mixture in portions which maintain the temperature under 28° C. The reaction is then heated to 60° C. with stirring until a clear solution is obtained. When the reaction is complete, it is cooled to and maintained at room temperature. Water is then added to quench the reaction. The resulting slurry is cooled in an ice bath and then filtered to obtain α-bromo-3-hydroxytricyclo [3.3.1.13,7]decane-1-acetic acid (Formula Q). See also Example 18 herein.

Source