Octahydro-1,4-methanonaphthalene → Exo-tricyclo[6.2.1.0(2.7)]undecane

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%).

1. customThe autoclave was closed
2. customsealed
3. filtrationfiltered
4. customto remove the catalyst
5. customThe filtrate separated into two layers
6. customThe MeOH layer (top layer) was isolated
7. concentrationconcentrated
8. customto give a residue, which
9. distillationwas distilled at reduced pressure

ORD record

ord-76944fac672d4c29a68933501960dba5

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084314B1