Acetyl bromide-α-D-glucose(I) as a sugar donor reacted with isoeugenol (II) to synthesize isoeugenol-2,3,4,6-tetra-O-acetyl-β-D-glucoside (Ⅲ) and isoeugenol-β-D-glucoside (Ⅳ). Phase transfer catalysis method and ionic liquid method were explored in the synthesis of compound III. The structures of the intermediates and target products were confirmed by 1HNMR, 13CNMR, IR and HRMS. Compound IV was added into cigarettes, and its transfer rate in the cigarette mainstream smoke was determined by gas chromatography-mass spectrometry (GC/MS). The results show that compound III can be obtained by the above two methods, and the ionic liquid method is better than the phase transfer catalysis method. The reaction conditions of ionic liquid method are as follows: 1-butyl-3-methyl-imidazonium bromide as catalyst, chloroform as solvent, sodium hydroxide aqueous solution as acid binding agent, n (I) : n (II) = 0.8 : 1, n (I) : n (1-butyl-3-methyl-imidazonium bromide) = 1 : 1, reaction at room temperature for 8 hours, yield of compound III is 56.8%. Compound III reacted in sodium methoxide/methanol solution to remove the tetraacetyl group to obtain compound IV in 87.6% yield. During cigarette smoking, the transfer rate of isoeugenol from the thermal decomposition of compound IV to the mainstream smoke particle phase is 3.2%.