Trimethyl orthoacetate → Methyl 4-iodo-3-nitrobenzoate

HRID 2044209Notes

Reaction equation

HRID 2044209 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[C:14](OC)(OC)(OC)C>>[CH3:14][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

3

Reactant 2

HCID 15050Trimethyl orthoacetate2×HCID 112085984-Iodo-3-nitrobenzoic acid

Product 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate

Procedure

We have also found an alternative, more efficient and simple method for esterification using trimethyl orthoacetate. The method involves dissolving 4-iodo-3-nitrobenzoic acid in trimethyl orthoacetate and refluxing the solution for 15 hours. Removal of the solvent under reduced pressure, gives 4-iodo-3-nitro benzoic methyl ester as a solid in almost quantitative yield (98%, 97% HPLC). It contains about 1.5% starting acid. Since the residual starting acid does not interfere in the next step, the material can be taken directly for the next stage. However, if required, the material can be further purified by crystallization from methanol and water with little loss of yield (95% Y, 98.3% HPLC).

Workup

  1. temperaturerefluxing the solution for 15 hours
  2. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-dfb89a21d04e442fb59a0bb6d3236ff8
Source dataset
uspto-grants-2013_11
Patent number
US08586792B2

Reaction notes

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