Citric Acid → HCID 20271475, Verbindung

HRID 485777

Reaktionsgleichung

Reaktionsgleichung von HRID 485777
CO[C:3]1C=C[C:6]([C:9](=O)[CH2:10][Br:11])=[CH:5][CH:4]=1.[CH2:13](O)/[CH:14]=C\CO.[C:19]([OH:31])(=[O:30])[CH2:20][C:21]([CH2:26][C:27]([OH:29])=O)(C(O)=O)O.[C:32]1(C=CC(O)=CC=1)O.C[O-].[Na+]>C(=O)(O)[O-].[Na+]>[CH3:32][O:29][C:27]1[CH:26]=[CH:21][C:20]([CH:19]2[O:30][CH:6]([CH2:9][CH2:10][Br:11])[CH:5]=[CH:4][CH2:3][O:31]2)=[CH:14][CH:13]=1

Komponenten

7

Edukt 5

HCID 311Citric AcidHCID 785HydroquinoneHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 6437902-Butene-1,4-diol, (2Z)-2×HCID 10942334Sodium Methoxide

Produkt 1

HCID 20271475HCID 20271475, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

1-(4'-methoxyphenyl)-2-bromo-1-ethanone (J. Org. Chem. Soc. 68, 868 (1946)) (6.90 g; 30 mmols), cis-2-butene-1,4-diol (90 ml), citric acid (0.60 g; 2.9 mmols) and hydroquinone (0.30 g; 2.7 mmols) are reacted at 70° C. for 12 hours under reduced pressure (0.15 mm Hg) by distillating off slowly 120 ml of liquid which is replaced, time by time, with cis-2-butene-1,4-diol (120 ml). The reaction mixture is cooled and sodium methoxide (0.20 g) is added. The reaction mixture is poured into a 10% aqueous solution of sodium bicarbonate (300 ml) and extracted with ethyl ether (3×90 ml).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl ether (3×90 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7d8a7e5318fd45fcb32eb908f9bb82f3
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537979

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