Conversion of fatty aldehyde dimethyl acetals to the corresponding alk-1-enyl methyl ethers (substituted vinyl ethers) during gas-liquid chromatography.
The behavior of palmitaldehyde and linolealdehyde and of their dimethyl acetals during gas-liquid chromatography on beta-cyclodextrin acetate (beta-CDX acetate) and ethylene glycol succinate polyester-phosphoric acid (EGSP) columns was studied. The aldehydes were well separated from their dimethyl acetals on the beta-CDX acetate column. However, on the EGSP column the retention times of palmitaldehyde and its dimethyl acetal were identical; a mixture of linolealdehyde and its dimethyl acetal gave a split peak. The aldehydes were recovered unchanged in 80-85% yield by preparative GLC from both columns, but the dimethyl acetals were quantitatively converted to the corresponding alk-1-enyl methyl ethers. The structure of these compounds was elucidated by infrared spectroscopy, mass spectrometry, and chemical means. Upon hydrolysis at low temperatures with 100% H(2)SO(4) they yielded the corresponding aldehydes, which were identified as 2,4-dinitrophenylhydrazones.
Mahadevan
V
V
University of Minnesota, The Hormel Institute, Austin, USA.
Viswanathan
C V
CV
Phillips
F
F
D000080:Acetals / Q000737:chemistry* / Q000302:isolation & purification; D000447:Aldehydes / Q000737:chemistry* / Q000302:isolation & purification; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D003505:Cyclodextrins; D005227:Fatty Acids / Q000737:chemistry* / Q000302:isolation & purification; D013058:Mass Spectrometry; D008738:Methyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013055:Spectrophotometry, Infrared
D000080:Acetals; D000447:Aldehydes; D003505:Cyclodextrins; D005227:Fatty Acids; D008738:Methyl Ethers; C001634:fatty aldehyde; C001647:hexadecanal