Regioselective reactions of phenol with formaldehyde by the use of dibutyltin oxide

Ninagawa, Akira; Ohnishi, Yoshinao; Takeuchi, Hideki; Matsuda, Haruo

doi:10.1002/marc.1985.030061201

Cited by 5 publications

(1 citation statement)

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“…3 2-Hydroxymethyl derivatives of phenols synthesised by reaction with formaldehyde under acidic conditions tend to polymerise and under base catalysis the reaction is partial requiring a chromatographic separation from the starting material, while under neutral conditions low conversions result, In all cases regiospecificity is absent. 4 Although some regiospecificity can be achieved, in the reaction of phenol and formaldehyde, by the use of dibutyltin oxide, 5 low conversions resulted. During exploratory work on the synthesis of isoanacardic aldehyde (2-hydroxy-4-pentadecylbenzaldehyde) by mild oxidation of the corresponding hydoxymethyl compound, we found that this could not be obtained regiospecifically from the reaction of 3-pentadecylphenol in alkaline conditions with aqueous formaldehyde.…”

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The synthesis of 2-hydroxymethyl derivatives of phenols

Payne

Tyman

Mehet

et al. 2006

Journal of Chemical Research

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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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confidence: 99%