Diethyl Ether → Methyl 4-iodobenzoate

HRID 1729

Reaktionsgleichung

Reaktionsgleichung von HRID 1729
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11]COCC.[N+](=C)=[N-]>O1CCCC1>[CH3:11][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 120854-Iodobenzoic acid

Produkt 1

HCID 69273Methyl 4-iodobenzoateAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Fifty (50) mmol (12.4 g) of commercially available 4-iodobenzoic acid was dissolved in 200 ml of tetrahydrofuran and then added to an ether solution containing freshly prepared diazomethane. The excess diazomethane was subsequently consumed by addition of glacial acetic acid and the resultant solution was concentrated in vacuo. The residue thus obtained was partitioned between ethyl acetate and saturated NaHCO3. The layers were separated and the aqueous phase was extracted with 100 ml of ethyl acetate. The organic extracts were combined, dried over Na2SO4, and concentrated in vacuo, yielding 13.01 grams (99.3% yield) of a yellow solid which melted at 111° C.

Aufarbeitung

  1. customThe excess diazomethane was subsequently consumed by addition of glacial acetic acid
  2. concentrationthe resultant solution was concentrated in vacuo
  3. customThe residue thus obtained
  4. customwas partitioned between ethyl acetate and saturated NaHCO3
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with 100 ml of ethyl acetate
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a23a2974ba3941e79b71f0f690cd1e1b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726312

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