Diethyl Ether → Methyl 4-iodobenzoate

HRID 1532971Notes

Reaction equation

HRID 1532971 reaction equation
[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

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 120854-Iodobenzoic acid

Product 1

HCID 69273Methyl 4-iodobenzoateYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 vacua, yielding 13.01 grams (99.3% yield) of a yellow solid which melted at 111° C.

Workup

  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 vacua

Sources & evidence

ORD record
ord-df77f444ad854ea988eb49ccae8b2fa7
Source dataset
uspto-grants-2001_03
Patent number
US06207670B1

Reaction notes

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