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The synthesis of deuterium labeled butylated hydroxytoluene (BHT)
Author(s) -
Mercer J. R.,
Wiebe L. I.
Publication year - 1978
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580140319
Subject(s) - butylated hydroxytoluene , chemistry , isobutylene , alkylation , trifluoroacetic acid , organic chemistry , medicinal chemistry , catalysis , antioxidant , copolymer , polymer
Attempts were made to synthesize 3,5‐di‐ t ‐butyl‐4‐hydroxytoluene containing a deuterium label. 1. p ‐cresol was alkylated with (D 8 )‐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 AlCl 3 . 4. BHT was treated with D 2 O and Pt 2 O in a catalytic exchange process. All methods gave labeled BHT but in all cases a mixture of isomers was found.