✍ Scribed by Davis, A. C. ;Hayes, B. T. ;Hunter, R. F.
No coin nor oath required. For personal study only.
The condensation of 3: 5: 3′: 5′‐tetrakis‐hydroxymethyl‐4: 4′‐dihydroxydiphenylmethane (I) with p‐substituted phenols provides a more convenient synthesis of bridged hexanuclear novolaks (II) than the reaction of formaldehyde with 2: 6‐dibenzylphenols under alkaline conditions, previously used for the synthesis of 4: 4′‐dihydroxy‐3: 5: 3′: 5′‐tetra‐(2″‐hydroxy‐3″: 5″‐dimethyl‐benzyl)diphenylmethane (II, R = R′ = Me). Debromination of 4: 4′‐dihydroxy‐3: 5: 3′: 5′‐tetra‐(5″‐bromo‐2″‐hydroxybenzyl)diphenylmethane (II, R = Br, R′ = H) by palladium and hydrogen furnished the unsubstituted hexanuclear novolak (II, R = R′ = H) which was finally obtained as a crystalline individual whose X‐ray diffraction pattern was quite different from that of the octamethyl compound. The X‐ray diffraction of the solvent‐free specimen of the latter proved quite distinct from that of the toluene‐adduct of the substance although two lines were common to both.
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## Abstract The bridged decanuclear novolak (**V**) has been synthesized rationally as a non‐crystalline chemical individual from 2: 6‐bis‐2′‐hydroxy‐5′‐methylbenzyl‐4‐bromophenol (**I**) by way of the dimethylol derivative (**II**) which on reaction with 2: 4‐xylenol furnished 2: 6‐bis‐2′‐hydroxy‐