2-Hydroxymethylphenols have been prepared in good yield by reduction with sodium borohydride of the precursor aldehydes, obtained regiospecifically from reaction of phenols with paraformaldehyde in toluene containing stannic chloride and tri-n-butylamine. By contrast, reaction of phenols with either paraformaldehyde under anhydrous conditions or with aqueous formaldehyde results in formation of both the hydroxymethyl and the bishydroxymethyl derivatives. Cyclic acetals of the precursor aldehydes are readily accessible.

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The isomeric 3-(hydroxyphenyl)propane-1, 2-diols have been synthesised from allylic precursors by epoxidation and cleavage. Several different methods have been examined for obtaining 1-(methoxyphenyl)propane-1, 3-diols. 2-(methoxyphenyl)propane-1, 3-diols and certain hydroxy analogues have been obtained from benzaldoximes converted by oxidation to methoxy-and benzyloxynitromethylbenzenes followed by hydroxymethylation with formaldehyde and catalytic hydrogenation.

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Alcohols Q 0230Long Chain Phenols. Part 41a. The Synthesis of 2-Hydroxymethyl Derivatives of Phenols. -Key step of the new approach to title compounds (IV) is the regiospecific reaction of phenols (I) with paraformaldehyde (II) in the presence of SnCl4 and NBu4. Cyclic acetals [cf. (VI)] of the intermediate aldehydes are readily accessible. -(PAYNE, P.; TYMAN*, J. H. P.; MEHET, S. K.; NINAGAWA, A.; J. Chem. Res. 2006, 6, 402-405; Dep. Chem., Brunel Univ., Uxbridge, Middlesex UB8 3PH, UK; Eng.) -H. Haber 46-104