Reaktion #1825

Reaktionsgleichung

diazomethane

4-iodobenzoic acid

ether

→

yellow solid

Ausbeute 99.3%

Methyl-4-iodobenzoate

Ausbeute 99.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe excess diazomethane was subsequently consumed by addition of glacial acetic acid
2. 2
   Einengenthe resultant solution was concentrated in vacuo
3. 3
   SonstigeThe residue thus obtained
4. 4
   Sonstigewas partitioned between ethyl acetate and saturated NaHCO3
5. 5
   SonstigeThe layers were separated
6. 6
   Extraktionthe aqueous phase was extracted with 100 ml of ethyl acetate
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle