関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Thionyl Chloride | HCID 24386 | — |
| 反応物 | Methyl p-coumarate | HCID 92203 | — |
| 反応物 | 4-(3-Butenyloxy)benzoic acid | HCID 544452 | — |
| 触媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 4-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoate | HCID 18329196 | 79.8% |
反応手順
8.7 g (0.045 mol) of 4-(but-3-enyloxy)-benzoic acid were treated with 76 ml of thionyl chloride and 2 drops of DMF and boiled under reflux for 3.5 hours. The excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum. The residual acid chloride was taken up in 10 ml of dichloromethane and slowly added dropwise at 0° C. to a mixture of 7.59 g (0,042 mol) of methyl 3-(4-hydroxyphenyl)-acrylate (Example 1) and 6 ml of triethylamine in 40 ml of dichloromethane. The batch was stirred at room temperature overnight. The white precipitate in the reaction mixture was dissolved by the addition of dichloromethane. The organic phase was washed repeatedly with water, dried over Na2SO4 and evaporated to dryness. For purification, the residue was chromatographed on silica gel with dichloromethane and subsequently recrystallized from ethanol. 12.65 g of 4-[(E)-2-methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoate were isolated as a white powder; phase succession (° C.): C 103 N138 l
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US06107427 |
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| 出典データセット | uspto-grants-2000_08 |
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| ORD ID | ord-595c5cbf2d974637b0268c6a69148604 |
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| 出典メモ | uspto-grants-2000_08 |
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