Catechol monobenzoate

Catechol monobenzoate has been synthesised effectively from phenol by treatment of 0-phenyl-N-benzoylhydroxylamine in trifluoroacetic acid during 1 hour at with trifluoromethanesulphonic acid and allowing the mixture to react for a further hour (ref.12). 

The rate of methanolysis of catechol monobenzoate is also enhanced and reaction probably proceeds by a mechanism analogous to that for the hydrolysis [24],... 

Capon, B., Gosh, B.C. The mechanism of the hydrolysis of phenyl salicylate and catechol monobenzoate in the presence and absence of borate ions. J. Chem. Soc. B 1966, 472-M78. 

The monobenzo-fused derivatives of 1,4-dioxin, 1,4-oxathiin and 1,4-dithiin, (345), (346) and (347), can all be prepared by base-catalyzed reaction between the appropriate 1,2-disubstituted benzene and an a-haloketal via an intermediate 2-alkoxy-2,3-dihydro derivative (348). The pyrolysis of the acetoxy derivative (349) at 450°C gives (345 80%) (67ZC152). 2-Hydroxy-2-phenyl-l,4-benzodioxane, from catechol and phenacyl bromide, is dehydrated to (345) by thionyl chloride in pyridine. 

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