Reacción #1825

Ecuación de reacción

diazomethane

4-iodobenzoic acid

ether

→

yellow solid

Rendimiento 99.3%

Methyl-4-iodobenzoate

Rendimiento 99.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe excess diazomethane was subsequently consumed by addition of glacial acetic acid
2. 2
   Concentraciónthe resultant solution was concentrated in vacuo
3. 3
   OtroThe residue thus obtained
4. 4
   Otrowas partitioned between ethyl acetate and saturated NaHCO3
5. 5
   OtroThe layers were separated
6. 6
   Extracciónthe aqueous phase was extracted with 100 ml of ethyl acetate
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente