Hydrochloric Acid → Methyl 2-heptyloxy-4-iodobenzoate

HRID 1171436

Reaktionsgleichung

Reaktionsgleichung von HRID 1171436
C(=O)([O-])[O-].[Cs+].[Cs+].[I:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([OH:18])[CH:9]=1.I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>CN(C=O)C>[CH2:20]([O:18][C:10]1[CH:9]=[C:8]([I:7])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 202741-IodoheptaneHCID 11380407Methyl 4-iodosalicylate

Produkt 1

HCID 68767792Methyl 2-heptyloxy-4-iodobenzoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of caesium carbonate (35.2 g, 108 mmol), methyl 4-iodo-2-hydroxybenzoate (25 g, 90 mmol), iodoheptane (19.2 ml, 117 mmol) in DMF (500 ml) is stirred for 10 hours at room temperature. The organic phase is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. After evaporation of the remainder of the iodoheptane by placing the oil obtained under vacuum produced by a rotary vane pump, 33.8 g (100%) of the expected compound are recovered in the form of a brown oil.

Aufarbeitung

  1. extractionThe desired product is extracted by addition of ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customAfter evaporation of the remainder of the iodoheptane
  7. customobtained under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0e218b050248476fb30901644d11cf9b
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829588B2

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