中文摘要：

对羟基苯甲醛是一种应用广泛的医药化工中间体,其骨架结构包含在多个药物中,且结构中的羟基与醛基具有良好的官能团易变性。对羟基苯甲醛的苯环2,3位并合不同大小脂肪环的结构可以作为相关药物全新结构类似物合成的关键中间体,然而此类结构（尤其是苯并七元脂肪环）的合成路线鲜见文献报道。为了合成抗癫痫药物沙芬酰胺类似物关键中间体,以2-羟基-5-甲基苯甲醛为原料,经羟基保护、Wittig反应、酯水解、烯烃还原、Friedel-Crafts酰化、羰基还原、醛基化、脱保护共8步反应（总收率3.6%）,首次制备了全新结构的4-羟基-6,7,8,9-四氢-5H-苯并[7]轮烯-1-甲醛,目标物和主要中间体结构经红外光谱、核磁共振氢谱、核磁共振碳谱和高分辨质谱表征。

英文摘要：

Para-hydroxybenzaldehyde（ PHBA） is a key intermediate,which is widely contained as a common moiety in many structures of drugs. PHBA can be readily transformed into new functionalities by adjusting the versatile hydroxy and aldehyde groups. The PHBA merged different cycloalkanes in the 2,3-positions of benzene ring are key intermediates for the synthesis of novel analogues of drugs containing PHBA moiety,but the synthetic methods of this kind of structures（ especially benzocycloheptane） are rarely reported. With the 2-hydroxy-5-methyl-benzaldehyde as a starting material,the synthetic method of the 4-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulene-1-carbaldehyde（ 3） was reported firstly,a key intermediate for the synthesis of the Safinamide analogs,through the reactions as follows： hydroxyl protection,Wittig reaction,ester hydrolysis,olefin reduction,FriedelCrafts acylation,carbonyl reduction,aldehyde formation,and deprotection（ a total yield of 3. 6%）. The target compound and key intermediates were confirmed by IR,1HNMR,13 CNMR and HRMS.