Six novel methyl cedrone O-substituted oximes were synthesized by the alkylation reaction using methyl cedrone oxime (16-methyl-2, 6, 6, 8-tetramethyl tricyclic-8-enone oxime) and halides as raw materials:16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-benzyl oxime (2a), 16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-(4-chlorobenzyl) oxime (2b), 16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-(4-cyanobenzyl) oxime (2c), 16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-(2, 6-dichlorobenzyl) oxime (2d), 16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-(4-tert-butylbenzyl) oxime (2e), 16-methyl-2, 6, 6, 8-tetramethyltricyclo-8-enone O-(o-fluorobenzyl) oxime (2f). The structures of the products were identified by FT-IR, GC-MS, 1H NMR and 13C NMR. Taking benzyl chloride as an example, the effects of solvents, the amount of tetrabutyl ammonium bromide(TBAB) and benzyl chloride, the reaction temperature and reaction time on the conversion and yield of 2a were discussed. The optimum condition was obtained as follows:toluene as solvent, n(methyl cedrone oxime):n(TBAB):n(benzyl chloride)=1.0:0.12:1.4, the reaction temperature was 70℃, the reaction time was 24 h. Under the optimal condition, the yield of product 2a was 78.10%, the yield of 2b-2f ranged from 58.91% to 71.36%.