Patent ID: 7524990

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 or hydroxyalkyl radicals having 1 to 4 carbon atoms, 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 acid halide or organic carboxylic acid anhydride, a ketene, or mixture of any two or of all three thereof, of the formula wherein R 12 and R 13 are the same or different and each is selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, aryl radicals bearing hydrogen or C 1 -C 10 alkyl groups substituted thereon, and mixtures thereof, X is 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 to 4 carbon, aryl radicals bearing substituents selected from the group consisting of hydrogen and one or more alkyl radicals, 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 an organic sulfonic acid of the formula R 14 —(SO 3 H) Q wherein Q is an integer selected from 1 to 4, R 14 is selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms, haloalkyl radicals of the formula C n H (2n+1)−z X z wherein n is 1 to 4, X is selected from the group consisting of F, Cl, Br, I, and mixtures thereof, and z ranges from 1 to 5, aryl radicals of the formula wherein R 15 , R 16 , R 17 , R 18 , and R 19 are the same or different and are selected from hydrogen and alkyl radicals having 1 to 20 carbon atoms, and mixtures thereof, to yield an acyl sulfonate of the formula or mixtures thereof, 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 or mixtures thereof, which is then aminated with an alkylamine of the formula wherein R 1 , R 2 , and R 3 are as previously defined to yield or mixtures thereof, which is then hydrolyzed with base to yield