Sodium Iodide → Carbonic acid, iodomethyl 4-nitrophenyl ester

HRID 2073330Notes

Reaction equation

HRID 2073330 reaction equation
[C:1](=[O:15])([O:12][CH2:13]Cl)[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[I-:16].[Na+]>CC(C)=O>[C:1](=[O:15])([O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)[O:12][CH2:13][I:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 2777826Chloromethyl 4-nitrophenyl carbonate

Product 1

HCID 15053075Carbonic acid, iodomethyl 4-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1.5 g of p-nitrophenyl chloromethyl carbonate in 100 ml of acetone was refluxed with 5 g of sodium iodide for 5 hours. The acetone was evaporated off. The residue taken in ether was washed successively with water, aqueous sodium bisulfite and water. After drying over sodium sulfate, the ether layer was evaporated to a light yellow oil weighing 1.75 g which was the pure iodomethyl carbonate. IR (film) 1777, 1522, 1202, 953, 867 cm-1NMR (CDCl3) 6.03 (s, 2H, CH2), 7.36 (d, J=10 Hz, 2H, aromatic) and 8.26 (d, J=10 Hz, 2H, aromatic).

Workup

  1. customThe acetone was evaporated off
  2. washwas washed successively with water, aqueous sodium bisulfite and water
  3. dry with materialAfter drying over sodium sulfate
  4. customthe ether layer was evaporated to a light yellow oil

Sources & evidence

ORD record
ord-ea94ec06cffe4f36afc89ebf4530eb77
Source dataset
uspto-grants-1990_04
Patent number
US04916230

Reaction notes

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