{"id":287,"date":"2011-01-24T16:45:00","date_gmt":"2011-01-24T16:45:00","guid":{"rendered":"https:\/\/psiconautica.org\/wordpress\/?p=287"},"modified":"2021-11-26T18:06:00","modified_gmt":"2021-11-26T18:06:00","slug":"345-trimethoxybenzaldehyde-synthesis","status":"publish","type":"post","link":"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/345-trimethoxybenzaldehyde-synthesis\/","title":{"rendered":"3,4,5-Trimethoxybenzaldehyde Synthesis"},"content":{"rendered":"
\n

3,4,5-Trimethoxybenzaldehyde Synthesis by Hest<\/h2>\n
\n

5-Bromovanillin<\/h3>\n

Add 15,2g vanilin and 17,6g Br2 to 75ml AcOH, let the solution stir 1 h. Pour out the solution in 250mL ice-water. filter off the product. Dry and recrystallise from ethanol. mp. 162\u00b0C. TLC Rf 0,47 EtOAC:P 1:1<\/p>\n

3,5-Dimethoxy-4-Hydroxybenzaldehyde (Syringaldehyde)<\/h3>\n

In a two-necked round-bottomed flask equipped with a Claisen, and a thermomether into the solution, is dissolved 4.9g Na in 100mL dry methanol. After distilling off 30ml methanol, a solution of 17,9g bromovanilin and 3g Cu(I)Br in 50mL DMF is added in one portion. The distillation is continued until the reaction mixture reaches 100\u00b0C (takes app. 1-1.5 h. total methanol distilled off is 80mL). The reaction mixture is poured into 200mL 3M HCL\/ice, extracted with 2*75mL EtOAc, the EtOAc is washed with 2*50mL water, dried with MgSO4 and evaporated. Mp.108\u00b0C (rec. from ethanol) TLC Rf 0,35 EtOAc:P 1:1<\/p>\n

3,4,5-trimethoxybenzaldehyde<\/h3>\n

10g 3,5-dimethoxy-4-hydroxy-benzaldehyde, 13.5g K2CO3 and 8.3g dimethylsulfate is dissolved in 80mL dry DMF, the solution is stirred for 2h and then poured into 800mL ice\/water, the product is filtered off and xtalised from cyclohexane.<\/p>\n

None of these reactions gives below 80% yield after the xtalisation.<\/p>\n

The condensation with MeNO2 and Ethylenediammonium diacetate gives ~30% yield.<\/p>\n

Reference:<\/b> Synthesis 308 (1983)<\/p>\n

\n","protected":false},"excerpt":{"rendered":"

3,4,5-Trimethoxybenzaldehyde Synthesis by Hest 5-Bromovanillin Add 15,2g vanilin and 17,6g Br2 to 75ml AcOH, let the solution stir 1 h. Pour out the solution in 250mL ice-water. filter off the product. Dry and recrystallise from ethanol. mp. 162\u00b0C. TLC Rf 0,47 EtOAC:P 1:1 3,5-Dimethoxy-4-Hydroxybenzaldehyde (Syringaldehyde) In a two-necked round-bottomed flask equipped with a Claisen, and […]<\/p>\n","protected":false},"author":1,"featured_media":1615,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[24],"tags":[],"class_list":["post-287","post","type-post","status-publish","format-standard","has-post-thumbnail","category-quimica-avanzada"],"yoast_head":"\n3,4,5-Trimethoxybenzaldehyde Synthesis - Psicon\u00e1utica<\/title>\n<meta name=\"robots\" content=\"noindex, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<meta property=\"og:locale\" content=\"es_ES\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"3,4,5-Trimethoxybenzaldehyde Synthesis - Psicon\u00e1utica\" \/>\n<meta property=\"og:description\" content=\"3,4,5-Trimethoxybenzaldehyde Synthesis by Hest 5-Bromovanillin Add 15,2g vanilin and 17,6g Br2 to 75ml AcOH, let the solution stir 1 h. Pour out the solution in 250mL ice-water. filter off the product. Dry and recrystallise from ethanol. mp. 162\u00b0C. 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