Synthesis of deuterated 5‐n‐alkylresorcinols

Abstract

Four alternative strategies for the preparation of deuterium poly-labelled 5-n-alkylresorcinols are explored. Ring-labelled 2 H 3 -alkylresorcinols synthesized by acidic H/D exchange are stable under electrospray ionization MS conditions but scrambling occurs in electron bombardment ionization MS. Side chain-labelled 2 H 4 -derivatives prepared by two different total synthesis approaches are contaminated by isotopologues with varying number of deuterium labels due to H/D redistribution and exchange during D 2 gas deuterogenation. The derivative carrying an x-2 H 3 label is isotopically pure and completely stable under all relevant analytical conditions encountered in quantitation work.