Paper
SYNTHESIS OF 2,4-DIMETHYL-5-IODOBENZALDEHYDE
Published Aug 1, 2002 · M. Akula, J. H. Zhang, G. Kabalka
Organic Preparations and Procedures International
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Abstract
Our recent efforts to synthesize radioiodinated benzylideneanabaseine 5 as a potential marker to detect small cell lung carcinoma' required large quantities of 2,4-dimethyl-5-iodobenzaldehyde (4) as starting material. Interestingly, the synthesis of 4 has never been reported. A number of attempts to prepare 4 from commercially available materials failed. These attempts included iodination of 2,4-dimethylbenzaldehyde using either iodine monochloride2 or NaI in the presence of chloramine-T? Vilsmeier formylation4 of 4-iodo-m-xylene, as well as a Gatterman aldehyde5 synthesis. We now report the synthesis of title compound 4 in three steps from 2,4dimethylbenzyl alcohol (1) in 5 1 % overall yield. Alcohol 1 was converted to acetate 2 by treatment with acetic anhydride and pyridine at room temperature for 24 h. Acetate 2 was then allowed to react with iodine monochloride in methylene chloride and acetic acid at room temperature for 15 h to obtain 2,4-dimethyl-5-iodobenzyl chloride, 3. Sommelet oxidation of benzyl chloride 3 to the requisite aldehyde 4 was accomplished using hexamethylenetetramine in acetic acid.
This study successfully synthesized 2,4-dimethyl-5-iodobenzaldehyde (4) from 2,4-dimethylbenzyl alcohol in 51% overall yield, providing a potential marker for small cell lung carcinoma detection.
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