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分别以(E)-1-苯基-1-丁烯-3-酮和4-苯基-2-丁酮为起始原料合成了3-羟基-4-苯基-2-丁酮。以(E)-1-苯基-1-丁烯-3-酮为起始原料,经过环氧化和还原两步反应得到产物;第1步环氧化反应,用双氧水作氧化剂,产率64%;第2步α,β-环氧酮在Pd/C催化作用下用甲酸还原,得到产物3-羟基-4-苯基-2-丁酮,产率67%;该路线总产率为43%。以4-苯基-2-丁酮为起始原料,经过烯醇硅醚中间体氧化得到产物;4-苯基-2-丁酮在六甲基二硅胺作用下与三甲基碘硅烷反应得到4-苯基-2-丁烯-2-基三甲基硅醚,产率为75%;第2步烯醇硅醚用间氯过氧苯甲酸氧化,得到产物3-羟基-4-苯基-2-丁酮,产率达71%;该路线总产率为53%。以(E)-1-苯基-1-丁烯-3-酮为起始原料的合成路线总产率略低,但操作简单,试剂价廉易得,是更为实用可行的合成路线。
3-Hydroxy-4-phenyl-2-butanone was synthesized starting from (E) -1-phenyl-1-buten-3-one and 4-phenyl-2-butanone respectively. (E) -1-phenyl-1-buten-3-one as the starting material, epoxidation and reduction two-step reaction products; the first step epoxidation, hydrogen peroxide as oxidant, the yield 64%. Step 2 α, β-epoxy ketone was reduced with formic acid under Pd / C catalysis to obtain the product 3-hydroxy-4-phenyl-2-butanone in 67% yield. The overall yield 43%. 4-phenyl-2-butanone is reacted with trimethylsilyl iodide under the action of hexamethyldisilazane by using 4-phenyl-2-butanone as a starting material and oxidizing the enol silyl ether intermediate to obtain the product; The reaction gave 4-phenyl-2-buten-2-yl trimethylsilyl ether in 75% yield; Step 2 Enolysyl ether was oxidized with m-chloroperoxybenzoic acid to give the product 3-hydroxy-4 -phenyl-2-butanone in a yield of 71%; the overall yield of this route was 53%. The yield of (E) -1-phenyl-1-buten-3-one is slightly lower than the total yield of the starting material. However, it is a more practical and feasible route because of its simple operation and low cost.