2,6-Bis(hydroxymethyl)-p-cresol

brown crystalline powder

2,6-Bis(hydroxymethyl)-p-cresol was used as a bridging ligand in binuclear oxovanadium(V) compound, which on exposure to white light and aerial oxygen forms an oligomeric compound.

The synthesis method for 2,6-Bis(hydroxymethyl)-p-cresol is as follows:
Aqueous formaldehyde (21.5 g, 37%) is added to a solution of p-cresol (10.8 g, 0.1 mol) and NaOH (5.0 g) in HO (20 mL).
The mixture is stirred at room temperature for 24 hours.
The mixture is filtered and washed with saturated aqueous NaCl (100 mL).
The resulting salt is dissolved in water (400 mL) and neutralized with acetic acid.
Pale pink crystals are obtained and filtered.
The crystals are washed with H2O and dissolved in hot ethyl acetate (40 mL).
The solution is dried over Na2SO4 and filtered while still hot.
The solution is concentrated to 27 mL and recrystallized overnight.
The product crystals are filtered and washed with cold ethyl acetate.
The crystals are air dried.

Rammal et al. report the study on the reaction between titanium(IV) alkoxides, known to be tetrameric [Ti4- (OR)16] (1) in the solid state, and an aromatic ligand such as 2,6-bis(hydroxymethyl)-p-cresol (BHMPC 2). Starting from the same planar tetrameric structure, a perfect geometrical match between octahedral edges of (1) and hydroxo moieties of (2) could be anticipated. Upon reaction of the ligand (2) with Ti(OEt)4, a new complex for which the tetrameric structure of (1) was preserved but with all edges occupied by sic molecules of (2) was obtained. The inorganic core of this tetranuclear complex (3) is composed of two μ3-oxo groups bridging the four titanium atoms. The tetranuclear titanium core is surrounded by six ligands (2) acting in groups of two, either as chelating, chelating-bridging, or tridentate units[1].

[1] Adel Rammal, Marc Henry, Frédéric Brisach. “Molecular Recognition of Titanium(IV) Alkoxides by 2,6-Bis(hydroxymethyl)-p-cresol in the Crystal Engineering of Hybrid OrganicInorganic Networks.” Journal of the American Chemical Society 123 23 (2001): 5612–5613.