Trimethylated resveratrol analogs increase the bioavailability of resveratrol while maintaining therapeutic cancer activities. Previously reported synthesis of 3,4′,5-trimethoxyresveratrol (3,4′,5-MeORSV) has involved the use of harmful reagents and the production of hazardous byproducts. In the current study, three synthetic schemes are presented that successfully produce 3,4′,5-MeORSV under mild reaction conditions with increasingly benign reagents. Two procedures follow classic Williamson ether synthesis, where stoichiometric amount of strong base generates phenolate anions, which then react with a methylating agent. Of these two procedures, one is carried out at room temperature in DMF, and the other in DMSO under reflux. An addnl. reaction scheme implements green chem. methods to methylate resveratrol with di-Me carbonate as a benign methylating agent and solvent in a solid/liquid phase transfer system. The "Green Star" metric is used to evaluate the degree of greenness of previously reported and novel reactions. It is reported that as 3,4′,5-MeORSV synthesis becomes greener, greater byproduct formation of the dimethylated product, pterostilbene, is observed