The synthesis of deuterium labeled butylated hydroxytoluene (BHT)

Abstract

AbstractAttempts were made to synthesize 3,5‐di‐t‐butyl‐4‐hydroxytoluene containing a deuterium label. 1. p‐cresol was alkylated with (D8)‐isobutylene. 2. 2,6‐di‐t‐butyl‐4‐hydroxytoluene was reacted with deuterated trifluoroacetic acid giving direct exchange. 3. 2,6‐dideutero‐4‐hydroxytoluene was synthesized and alkylated with isobutylene and with 2‐methyl‐2‐chloropropane and AlCl3. 4. BHT was treated with D2O and Pt2O in a catalytic exchange process. All methods gave labeled BHT but in all cases a mixture of isomers was found.