Reaction #2201715

Reaction equation

hydrogen

octahydro-2-trifluormethyl-1,4-methanonaphthalene

hydrogen

→

decahydro-2-trifluoromethyl-1,4-methanonaphthalene

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe autoclave is closed
2. 2
   Othersealed
3. 3
   workup.DISTILLATIONThe decahydro-2-trifluormethyl-1,4-methanonaphthalene product is purified by distillation at reduced pressure
4. 4
   workup.ADDITIONThe distilled product is then treated with concentrated sulfuric acid

Procedure

A 400 ml autoclave is charged with 177 g of the thus purified octahydro-2-trifluormethyl-1,4-methanonaphthalene, methanol (100 ml, Burdick & Jackson, HPLC grade), and palladium on activated carbon (1.5 g containing 10% Pd, Alfa products, powder). The autoclave is closed and sealed, then it is shaken under 50 psig hydrogen pressure for 20 minutes at room temperature. The hydrogen pressure is increased to 200 psig for 10 minutes at room temperature followed by 600 psig at 70° C. for 45 minutes. The decahydro-2-trifluormethyl-1,4-methanonaphthalene product is purified by distillation at reduced pressure. The distilled product is then treated with concentrated sulfuric acid followed by silica gel treatment similar to what described in the example 2.

Source