Synthesis of the perdeuterated cellulose solvents <i>N</i>‐methylmorpholine <i>N</i>‐oxide (NMMO‐d₁₁) and <i>N,N</i>‐dimethylacetamide (DMAc‐d₉)

Abstract

Abstract The synthesis of the perdeuterated cellulose solvents NMMO‐d 11 (9) and N , N ‐dimethylacetamide‐d 9 (14) is described. NMMO‐d 11 was obtained according to a five‐step approach from non‐labeled diglycolic acid (1) via diethylene glycole‐d 8 (4) and its bis‐tosylate (5), which underwent cyclization with benzylamine to N ‐benzylmorpholine (6). The removal of the benzyl protecting group, methylation and N ‐oxidation completed the synthesis. DMAc‐d 9 (14) was obtained from deuterated acetic acid (10) and dimethylamine–carbon dioxide complex (17) with acidic alumina as the catalyst according to a solvent‐free gas–solid reaction. Copyright © 2008 John Wiley &amp; Sons, Ltd.