Transformation of Alkyl Halides to Aldehydes Having Two Additional Carbon Atoms
Methyl 3-oxo-4-phenylbutanoate (6) reacts with alkyl halides (1a-g) in the presence of NaH/benzene to furnish alkylated β-keto esters (2a-g).Hydrolysis of 2a-g gives benzyl ketones (3a-g), which on reduction with sodium borohydride give the homobenzylic alcohols (4a-g).The alcohols (4a-g) are readily fragmented to aldehydes (5a-g) on heating with lead tetraacetate/iodine.
Shankaran, K.,Talekar, D. G.,Rao, A. S.
p. 408 - 410
(2007/10/02)
SYNTHESIS OF ALDEHYDES AND BENZYLKETONES THROUGH FRAGMENTATION OF HOMOBENZYLIC ALCOHOLS
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Shankaran, R.,Talekar, D. G.,Rao, A. S.
p. 141 - 150
(2007/10/02)
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