In order to improve the stability of guaiacol, a glycosylation reaction between 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide (Ⅱ) and guaiacol(Ⅰ) led to guaiacol-2,3,4,6-tetra-O-acetyl-β-D-glucoside (Ⅲ) by silver salt method, phase transfer catalysis and ionic liquid method, respectively. Finally, guaiacol-β-D-glucoside (Ⅳ) was obtained by deacetylation of glucoside III. The structures of the intermediates and products were confirmed by 1HNMR, 13CNMR, IR and HRMS. The thermal stability of the target product (Ⅳ) was studied by thermogravimetric analysis and differential scanning calorimetry (TG-DSC). The flavoring effect of glycoside IV was investigated by sensory evaluation. The results show that glucoside Ⅲ synthesized by three above-mentioned methods was target product, ionic liquid method is better than phase transfer catalysis and silver salt method. The reaction conditions of ionic liquid method were as follows: 1-butyl-3-methylimidazole tetrafluoroborate ([bmim] BF4) as catalyst, anhydrous potassium carbonate as acid binding agent, dichloromethane as solvent, n (guaiacol) : n (bromotetraacetylglucose) = 1.0 :1.0, reaction at room temperature for 4 hours, and the yield of compound III was 52.6%. Compound III was deacetylated in sodium methoxide/methanol system to obtain the target product glycoside (Ⅳ). TG-DSC study showed that guaiacol- β- D-glucoside has good thermal stability below 228 ℃. Adding glycoside Ⅳ to cigarettes can improve the aroma quality.