Methyl iodide → 4-Hydroxyisophthalic acid 1-ethyl ester 3-methyl ester

HRID 423250Notes

Reaction equation

HRID 423250 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:13]=[CH:12][C:11]([OH:14])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2].CI.[C:18](=O)([O-])O.[Na+]>CN(C=O)C>[CH3:18][O:9][C:8](=[O:10])[C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][C:11]=1[OH:14])[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 539597625-(Ethoxycarbonyl)-2-hydroxybenzoic acid

Product 1

HCID 586297364-Hydroxyisophthalic acid 1-ethyl ester 3-methyl esterYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxyisophthalic acid 1-ethyl ester (4.51 g) in DMF (36 mL) were added methyl iodide (3.66 g) and sodium hydrogen carbonate (2.16 g). The mixture was stirred at 60° C. for 2 hours and then allowed to stand for cooling down to room temperature. The resulting precipitated solid formed upon addition of water was filtered off to give the title compound (4.20 g).

Workup

  1. temperaturefor cooling down to room temperature
  2. customThe resulting precipitated solid
  3. customformed upon addition of water
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-d8b241858f8e42eca531cd47128c03fc
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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