Patent ID: 7538251

Claim:
A method for the synthesis of severely sterically hindered secondary aminoether alcohols of the formula wherein R 1 and R 2 are each selected from the group consisting of alkyl, hydroxylalkyl radicals having 1 to 4 carbon atoms or in combination with the carbon atom to which they are attached they form a cycloalkyl group having 3 to 8 carbon atoms, and R 3 is selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals having 1 to 4 carbon atoms, and mixtures thereof, and R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are the same or different and are selected from the group consisting of hydrogen, alkyl and hydroxyalkyl radicals having 1 to 4 carbons provided that at least one of R 4 or R 5 bonded to the carbon atom directly bonded to the nitrogen atom is an alkyl or hydroxyalkyl radical when R 3 is hydrogen, the process involving reacting an organic carboxylic acid halide, an organic carboxylic acid anhydride, a ketene, or a mixture of any two or of all three thereof, of the formula wherein R 12 and R 13 are the same or different and are selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, aryl radicals bearing hydrogen or C 1 to C 10 alkyl radicals substituted thereon, and mixtures thereof, X is a halogen selected from the group consisting of F, Cl, Br, I, and mixtures thereof, and R x and R y are the same or different and are selected from the group consisting of hydrogen, alkyl radicals having 1-4 carbons, aryl radicals, aryl radicals bearing substituents selected from the group consisting of hydrogen and one or more alkyl radicals having 1 to 10 carbons, and mixtures thereof, or R x and R y in combination with the carbon to which they are attached form a cycloalkyl radical having 3 to 8 carbons, with 50% sulfuric acid to fuming sulfuric acid to yield monoacylsulfate (3) and/or diacylsulfate (4) of the formula which is then reacted with a dioxane of the formula wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are the same or different and are selected from hydrogen, alkyl and hydroxyalkyl radicals having 1 to 4 carbons to yield products of the structure 6 and/or 7: and mixtures thereof, which are then aminated with an alkyl amine of the formula wherein R 1 , R 2 and R 3 are as previously defined to yield material of the general formula 9 or mixtures thereof, which is then hydrolyzed with base to yield product (1).