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

HRID 1872308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872308
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].S(Cl)(Cl)=O.O[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C=O)C.ClCCl>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 92203Methyl p-coumarateHCID 5444524-(3-Butenyloxy)benzoic acid

Produkt 1

HCID 183291964-[(e)-2-Methoxycarbonyl-vinyl]-phenyl 4-(but-3-enyloxy)-benzoateAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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

Aufarbeitung

  1. temperatureunder reflux for 3.5 hours
  2. customThe excess thionyl chloride was completely removed firstly in a water-jet vacuum and subsequently in a high vacuum
  3. washThe organic phase was washed repeatedly with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customFor purification
  7. customthe residue was chromatographed on silica gel with dichloromethane
  8. customsubsequently recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-595c5cbf2d974637b0268c6a69148604
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107427

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