Preparation of 2-t-butyl-4-alkoxy- and 4-hydroxyphenols
AssigneeUop LLC
InventorsBruce E. Firth, Terry J. Rosen
Life of this patent
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Abstract
Tertiary alkyl phenyl ethers may be induced to undergo thermal rearrangement on an alumina catalyst to afford the isomeric ortho-t-alkylphenol. Such rearrangement generally occurs under milder conditions than does the alkylation of a phenol with an olefin using the same alumina as an alkylating catalyst. The rearrangement remains regioselective even when the phenyl ring bears an alkoxy group, hence affords a good preparative route to such materials as 2-t-butyl-4-methoxyphenol.
Claims17
A method of rearranging a t-alkyl 4-alkoxyphenyl ether or a t-alkyl-4-hydroxyphenyl ether to a 2-t-alkyl-4-alkoxyphenol or a 2-t-alkyl-4-hydroxyphenol, respectively, comprising heating said ether in contact with an alumina selected from the group consisting of alumina, aluminas containing an alkali metal cation in the matrix, lithiated alumina, and silica-alumina at a temperature from about 65.degree. C. to about 150.degree. C. and recovering the formed phenol.
A method of ortho-alkylating a 4-alkoxyphenol or 4-hydroxyphenol comprising converting the phenol to a t-alkyl phenyl ether, heating the ether in contact with an alumina selected from the group consisting of alumina, aluminas containing an alkali metal cation in the matrix, lithiated alumina, and silica-alumina at a temperature from about 65.degree. C. to about 150.degree. C., and recovering the formed 2-t-alkyl-4-alkoxyphenol or 2-t-alkyl-4-hydroxyphenol, respectively.
Dependencies are inferred from the claim text.