Hydrochloric Acid → Methyl 2-heptyloxy-4-iodobenzoate

HRID 1171430

Reaktionsgleichung

Reaktionsgleichung von HRID 1171430
[OH:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](I)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 68767792Methyl 2-heptyloxy-4-iodobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-hydroxy-4-iodobenzoate (25 g, 90 mmol), caesium carbonate (35.2 g, 108 mmol) and n-heptyl iodide (19.2 ml, 117 mmol), in 500 ml of dimethylformamide (DMF) is stirred for 10 hours at room temperature. The solution is neutralized by addition of 2N hydrochloric acid solution. 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 solvent, 33.84 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 solvent, 33.84 g (100%) of the expected compound
  7. customare recovered in the form of a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-9025c5aebbdb4754af04ea06696318b4
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829588B2

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