Oxidation with chromium(VI) complexes: Difference between revisions

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===Example Procedure<ref>Guziec, F. S., Jr.; Luzzio, F. A. ''J. Org. Chem.'', '''1982''', ''47'', 1787.</ref>===

<span style="float:right;padding-right:50px;padding-top:10px;">'''''(10)'''''</span><center>[[File:ChroEx.png]]</center>

To a solution of ''p''-(3-hydroxypropyl)benzyl alcohol (165 mg, 1 mmol) in N,N-dimethylformamide (3 mL) was added imidazolium dichromate (705 mg, 2 mmol) and the mixture was stirred at room temperature (4 hours). After completion of the reaction, water (30 mL) was added to the reaction mixture and the product was extracted three times with diethyl ether. The ether extracts were washed with water and aqueous NaHCO3NaHCO₃, dried over anhydrous MgSO4MgSO₄, and evaporated to dryness. The crude product was subjected to silica gel column chromatography with dichloromethane-ethyl acetate (4:1) as eluent to yield ''p''-(3-hydroxypropyl)benzaldehyde (112 mg, 68%);: ¹H NMR (CDCl₃): δ1δ 1.8–2.3 (m, 2 H), 2.77 (s, 1 H), 2.93 (t, 2 H, J = 6 Hz), 3.80 (t, 2 H, J = 6 Hz), 7.4–7.98 (m, 4 H), 10.10 (s, 1 H). IR (film) 1700 cm–1cm^–1. δ and 3-(4-Formylphenyl)propanal (4 mg, 3%): ¹H NMR (CDCl₃): =δ 2.45–3.21 (m, 4 H), 7.31–7.85 (m, 4 H), 9.81 (s, 1 H), 9.95 (s, 1 H).

==References==