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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 6
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Original Articles

A Facile Deprotection of Dithioacetals by FeCl3/KI

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Pages 879-883 | Received 21 Feb 2002, Published online: 17 Aug 2006

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  • General Procedure: A mixture of dithioacetal of p-methoxy benzaldehyde (212 mg, 1 mmol), FeCl3 (162 mg, 1 mmol) and KI (166 mg, 1 mmol) was refluxed in methanol. Progress of the reaction was monitored by TLC. After the completion of the reaction, methanol was removed under reduced pressure and residue was extracted in ether. The ether extract was dried over anhydrous Na2SO4 and the organic layer was filtered. Evaporation of the solvent under reduced pressure furnished pure anisaldehyde (122 mg, 90%). IR (film, cm−1) : ν = 3009, 2739, 1684, 1578, 1511, 1461. 1H NMR (CDCl3, 200 MHz): δ = 3.89 (s, 3H), 7.01 (d, J = 8.7 Hz, 2H), 7.85 (d, J = 8.7 Hz, 2H), 9.90 (s, 1H). 13C NMR (CDCl3, 50 MHz): δ = 190.6, 164.4, 131.7, 129.7, 114.1, 55.3

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