Alkyl chlororesorcinols

Primary alkyl phenols have been prepared by the reduction of acyl phenols 1 by the demethylation of the corresponding ethers 12 by the diazotization of the corresponding amines 3 and by the alkali fusion of sulfonates.4 Alkyl resorcinols have been prepared by the reduction of acyl resorcinols.1 5 6 Alkyl chlororesorcinols have been prepared from the corresponding acyl chlororesorcinols by reduction.7... 

The synthesis of 2,4-dihydroxyacetophenone [89-84-9] (21) by acylation reactions of resorcinol has been extensively studied. The reaction is performed using acetic anhydride (104), acetyl chloride (105), or acetic acid (106). The esterification of resorcinol by acetic anhydride followed by the isomerization of the diacetate intermediate has also been described in the presence of zinc chloride (107). Alkylation of resorcinol can be carried out using ethers (108), olefins (109), or alcohols (110). The catalysts which are generally used include sulfuric acid, phosphoric and polyphosphoric acids, acidic resins, or aluminum and iron derivatives. 2-Chlororesorcinol [6201-65-1] (22) is obtained by a sulfonation—chloration—desulfonation technique (111). 1,2,4-Trihydroxybenzene [533-73-3] (23) is obtained by hydroxylation of resorcinol using hydrogen peroxide (112) or peracids (113). 

Other ketones may be reduced by this same procedure. The submitters report that the following have been reduced with yields of 70-90 per cent 0- and p-butyryl phenols, 0- and p-valeryl phenols, 0- and />-caproyl phenols, 0- and />-heptanoyl phenols, 0- and -octanoyl phenols, o- and />-pelargonyl phenols, o- and />-undecylyl phenols. The same procedure applies to acyl resorcinols and acyl chlororesorcinols. Caproyl and octanoyl resorcinols reduce to the corresponding alkyl derivatives in yields of 70-80 per cent. Butyryl, valeryl, caproyl, heptanoyl,... 

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