Abstract
Selective synthesis of 4-(hydroxymethyl)phenol ( I) from phenol and formaldehyde is successfully achieved in 0.75 N aqueous sodium hydroxide solutions at 30 °C by use of β-cyclodextrin (β-CyD) as catalyst. The molar ratio of I to 2-(hydroxymethyl)phenol, formed as a byproduct, is 5.3 at a 0.4 M concentration of β-CyD (the selectivity is 84% for I). In its absence, the molar ratio is only 1.5. β-CyD accelerates the formation of I by 28-fold. The catalytic effect of α-CyD is much smaller, whereas γ-CyD decreases the selectivity. The selective catalysis by β-CyD is ascribed to the formation of inclusion complexes of β-CyD both with phenolate and with formaldehyde.
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