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HRID 1872308作成日:2026年10月25日

Triethylamine → 4-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoate

https://huagongshe.com/reaction/1872308

反応式

関与物質

役割名称HCID仕込み量
反応物TriethylamineHCID 8471—
反応物Thionyl ChlorideHCID 24386—
反応物Methyl p-coumarateHCID 92203—
反応物4-(3-Butenyloxy)benzoic acidHCID 544452—
触媒DimethylformamideHCID 6228—
溶媒DichloromethaneHCID 6344—
生成物4-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoateHCID 1832919679.8%

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

DOI10.6084/m9.figshare.5104873.v1
特許番号US06107427
出典データセットuspto-grants-2000_08
ORD IDord-595c5cbf2d974637b0268c6a69148604
出典メモuspto-grants-2000_08