八氢-2H-1-苯并吡喃-2-酮的合成及在卷烟加香中的应用

Synthesis of Octahydro-2H-1-benzopyran-2-one and its Application in Tobacco Flavoring

碳酸钾催化环己酮和丙烯酸甲酯Michael加成制得3-(2-氧代环己基)丙酸甲酯,后在碱性条件下用硼氢化钠还原酮羰基,酸化环化即制得八氢-2H-1-苯并吡喃-2-酮,总收率为55%。将其应用于卷烟加香,证实它是一种理想的烟用香料添加剂。

Methyl 3-（2-oxo-cyclohexyl）propionate is synthesized through the Michael addition of cyclohexanone to methyl acrylate catalyzed by anhydrous potassium carbonate. It is converted to octahydro-2H-1-benzopyran-2-one after being hydrolyzed, reduced the to δ-hydroxy group with NaBH 4 and acidified. Total yield is 55%. Octahydro-2H-1-benzopyran-2-one can be used as a satisfactory tobacco additive is proved.