3-alkylated-5,5',6,6', 7, 7', 8, 8'--octahydro-2, 2'-binaphthols and 3, 3'-dialkylated- 5, 5', 6, 6', 7, 7', 8, 8'-octahydro--2, 2'-binaphthols and processes for making

DETAILED DESCRIPTION OF THE INVENTION The alkylated 5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthols of this invention may be prepared by alkylation of 5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol in the presence of a catalyst, as shown below.
##STR00003## The starting material, 5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol, can be obtained by the hydrogenation of 2,2'-binaphthol using a PtO.
sub.
2 catalyst, as described in Tetrahedron Lett.
1997, 5273.
The first process aspect of the present invention is a process for making alkylated 5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthols by an acid-catalyzed, selective alkylation of 5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol by alkenes or cycloalkenes in the presence of an acid catalyst.
The acid catalyst may be a Lewis acid or a protic acid.
Suitable catalysts include the following: AlCl.
sub.
3, trifluoromethanesulfonic acid, tosylic acid, phosphotungstic acid, silicotungstic acid, phosphomolybdic acid, zirconium or aluminum triflate, polymeric perfluorinated sulfonic acid (such as the material sold by DuPont as Nafion.
RTM.
) and polymeric sulfonic acid (such as the material sold by Aldrich as Amberlyst.
RTM.
15 ion-exchange resin or the material sold by Dow as Dowex 32.
RTM.
).
Phosphotungstic acid is preferred.
The alkenes include monoethylenically unsaturated compounds containing from 3 to 20 carbons, such as propylene, butene, pentene, hexene, cyclopentene, cyclohexene, etc.
The reaction may be carried out at 20.
degree.
C.
to 220.
degree.
C.
, preferably at 90.
degree.
C.
to 180.
degree.
C.
, when mono-substituted or 1,2-disubstituted alkenes are utilized as alkylating reagents, and 40.
degree.
C.
to 90.
degree.
C.
when 1,1-disubstituted, tri-substituted, tetra-substituted or aryl-substituted alkenes are utilized as alkylating reagents.
The alkylation reaction may be carried out neat (without solvent) or in inert solvents such as nitromethane, methylene chloride, dichloroethane, chlorobenzene, dichlorobenzene, nitrobenzene or a combination of these solvents