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The synthesis of 3,4‐ 2 H 2 ‐3Z‐hexenal and 6,6,6‐ 2 H 3 ‐3Z‐hexenal
Author(s) -
Fielder Simon,
Rowan Daryl D.
Publication year - 1995
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.2580360510
Subject(s) - chemistry , yield (engineering) , aldehyde , solvent , catalysis , freon , organic chemistry , materials science , metallurgy
6,6,6‐ 2 H 3 ‐3Z‐Hexenal (3b) has been prepared in 89% yield and in greater than 94% purity by the oxidation of 6,6,6‐ 2 H 3 ‐3Z‐Hexen‐1‐ol (2b) with the Dess/Martin periodinane (1) in fluorotrichloromethane (freon 11). Use of the freon solvent greatly improved the recovery of this volatile aldehyde. Similarly the oxidation of 3,4‐ 2 H 2 ‐3Z‐hexen‐1‐ol (5) yielded 3,4‐ 2 H 2 ‐3Z‐hexenal (6) in a 92% isolated yield with a purity of greater than 99%. 3,4‐ 2 H 2 ‐3Z‐Hexen‐1‐ol (5) was prepared in 87% by the catalytic deuterogenation of 3‐hexyn‐1‐o1 (4) in an improved synthetic procedure.