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Hydrolysis of a dibromomethyl arene; 2-Hydroxyisophthalaldehyde

SyntheticPage 415
DOI: 10.1039/SP415
Submitted May 27, 2010, published May 27, 2010
David Fox (d.j.fox@warwick.ac.uk)
A contribution from Fox Group, Warwick University


			Reaction Scheme: Hydrolysis of a dibromomethyl arene

Chemicals Used

2,6-Bis(dibromomethyl)anisole synthesis
90% HCHO(aq)

Procedure

2,6-Bis(dibromomethyl)anisole (13.42 g, 30 mmol) was suspended in 90% HCHO(aq) (70 ml) and heated at reflux for 16 hours.  The deep-red coloured solution was allowed to cool and was then poured into cold water (200 ml).  The precipitate was collected via filtration and then recrystallised from water to give 2,6-diformylphenol as white crystals (2.70g, 60%). 

Author's Comments

Data

mp 124 oC (ref 123 oC); νmax (KBr)/cm-1 3436 (OH), 1681 (C=O); δH (200MHz, CDCl3) 11.68 (1H, s, OH), 10.26 (2H, s, CHO), 7.98 (2H, d, J 8.0, m-CH), 7.15 (1H, t, J 8.0, p-CH); m/z (APCI-) 149 (100%, (M-H)-).

Lead Reference

S. Labidalle, E. Jean, H. Moskowitz, M. Miocque and C. Thal, Tetrahedron Lett., 1981, 22, 2869-2870.

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Post new comment
  • Guest Jussi HelminenOct 10 2011 11:57PMA typo

    There must be a typo in the procedure, as 90% HCHO(aq) would be 90% aqueous formaldehyde solution, which in practice doesn't exist.

    • Guest milkshakenOct 13 2013 7:14AMtypo

      most likely, this was supposed to be 90% formic acid (which makes sense, for a solvolytic reaction)

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