Dopac → HCID 19001625, Verbindung

HRID 486914

Reaktionsgleichung

Reaktionsgleichung von HRID 486914
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[OH:8].[C:13](OC=C)(=O)[CH3:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O1CCCC1.[Hg]=O.O>[OH:12][CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][CH:13]([CH3:14])[O:1][C:2]=2[CH:3]=1

Komponenten

10

Edukt 4

HCID 547DopacHCID 7904Vinyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 19001625HCID 19001625, VerbindungAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 30856Mercuric oxideKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 1.0 g of 3,4-dihydroxyphenylacetic acid, 1.4 g of vinyl acetate, 6 mg of mercury oxide (yellow) and 0.03 ml of boron fluoride/ethyl etherate in 9 ml of toluene was stirred at room temperature for 14 h. The reaction mixture was diluted with ethyl acetate and washed with water and an aqueous common salt solution. The organic layer was dried over magnesium sulfate and the solvent was distilled off. An oil thus obtained was dissolved in 10 ml of tetrahydrofuran and the solution was added dropwise to a suspension of 0.5 g of lithium aluminum hydride in tetrahydrofuran under cooling with ice. The mixture was stirred at room temperature for 1 h. 0.5 ml of water, then 0.5 ml of a 15% aqueous sodium hydroxide solution and finally 1.5 ml of water were added thereto and an insoluble matter was filtered off. The filtrate was concentrated and treated according to silica gel column chromatography (ethyl acetate/hexane=1:1) to obtain 0.8 g of the intended compound in the form of a colorless oil.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customAn oil thus obtained
  5. temperatureunder cooling with ice
  6. stirringThe mixture was stirred at room temperature for 1 h
  7. filtrationan insoluble matter was filtered off
  8. concentrationThe filtrate was concentrated
  9. additiontreated

Quellen und Nachweise

ORD-Eintrag
ord-a1bc0894b2d24344aadb103d3b7055ea
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292901

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