Reaction #7366

Reaction equation

hydrogen

octahydro-1,4-methanonaphthalene

hydrogen

→

decahydro-1,4-methanonaphthalene

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe autoclave was closed
2. 2
   Othersealed
3. 3
   Filtrationfiltered
4. 4
   Otherto remove the catalyst
5. 5
   OtherThe filtrate separated into two layers
6. 6
   OtherThe MeOH layer (top layer) was isolated
7. 7
   Concentrationconcentrated
8. 8
   Otherto give a residue, which
9. 9
   workup.DISTILLATIONwas distilled at reduced pressure

Procedure

A 400 ml autoclave was charged with octahydro-1,4-methanonaphthalene (122 g, prepared as described above), methanol (100 ml, Burdick & Jackson, HPLC grade), and palladium on activated carbon (1.5 g containing 10% Pd, Alfa products, powder). The autoclave was closed and sealed, then shaken under 50 psig hydrogen pressure for 20 minutes at room temperature. The hydrogen pressure was increased to 200 psig for 10 minutes at room temperature followed by 600 psig at 70° C. for 45 minutes. The reaction mixtures from three identical reactions were combined and filtered to remove the catalyst. The filtrate separated into two layers. The MeOH layer (top layer) was isolated and concentrated to give a residue, which was combined with product layer (the bottom layer). The combined crude product was distilled at reduced pressure to give decahydro-1,4-methanonaphthalene (318.6 g, bp 71–73° C./0.2 Torr, yield 86%).

Source