Acetone → HCID 57554489, Verbindung

HRID 551917

Reaktionsgleichung

Reaktionsgleichung von HRID 551917
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].[CH3:14][C:15]([CH3:17])=O>C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>[CH3:14][C:15]1([CH3:17])[O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[C:11](=[O:13])[O:12]1

Komponenten

5

Edukt 2

HCID 180AcetoneHCID 124904-Hydroxyisophthalic acid

Produkt 1

HCID 57554489HCID 57554489, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6422Trifluoroacetic acidLösungsmittelHCID 9845Trifluoroacetic anhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of 4-hydroxyisophtalic acid (Aldrich, 5.0 g, 27.5 mmol) in acetone (10 mL), TFA (30 mL) and TFAA (10 mL) was heated at 100° C. for 24 hrs. The reaction mixture was concentrated under reduced pressure. The residue was taken up with an aqueous solution of HCl (100 mL, 1N) and extracted with EtOAc (3×200 L); The combined organic layers were dried over MgSO4 and the solvents were removed under reduced: pressure. The crude compound was recrystallized in Et2O (50 mL) to give 4.67 g (77%) of the title compound as a beige powder. 1H NMR (DMSO-d6) δ: 8.37 (d J=1.9 Hz, 1H), 8.19 (dd, J=2.2 and 8.7 Hz, 1H), 7.23 (d, J=8.3 Hz, 1H), 1.72 (s, 6H). HPLC, Rt: 2.40 min (purity: 95.7%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc (3×200 L)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvents were removed
  5. customThe crude compound was recrystallized in Et2O (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5239bc217de14bc19f5e1c209b28bbc8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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