3 -Acetoxy -5 -methoxy toluene

Z)-2-Aceto y-l-[(/R, 2R )-trans-2-le l-butyldimetliylsilyloxy-l-cyclohexy/oxy]-l-buten-3-one A solution of 1.8 g (11.4 mmol) of tr n.r-3-acetoxy-4-methoxy-3-buten-2-one, 2.4 g (10.4 mmol) of ( R, 2R )-trans-2-rm-butyldimethylsilyloxy-1-cydohexanol obtained above, and 0.3 g (1.2 mmol) of pyridinium 4-toluene-sulfonate in 50 mL of benzene is refluxed for 30 h with continuous removal of CH, OH using a Dean-Stark trap containing 4 A molecular sieves. The reaction mixture is concentrated in vacuo and chromatographed (silica gel, EtOAc/hexane 3 7) yield 2.6 g (70%). 

Porcine pancreatic lipase immobilized in microemulsion-based gels was used for the regioselective hydrolysis of perpropanoates of di-/trihydroxylic phenols in benzene. For example, 2,6-dipropanoyloxy toluene was converted to 2-hydroxy-6-propanoyloxy toluene in 40% yield [42]. The lipase from CCL deacylates the acetoxy functionality of aUcyl acetoxybenzoates faster than the benzoyloxy one. The difference in reactivity between the two ester functionalities is less in aryl than in alkyl acetoxybenzoates and a methoxy group in the meta position of the aryl group reverses the reactivity [43]. 

---