Isopropyl iodide → HCID 23072939, compound

HRID 732522Notes

Reaction equation

HRID 732522 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.I[CH:17]([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CC(C)=O.C(OCC)(=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH:17]([CH3:19])[CH3:18])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

7

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 23072939HCID 23072939, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir 5-hydroxy-isophthalic acid dimethyl ester (4 g, 19.0 mmol), 2-iodopropane (10.2 mL, 101 mmol), and potassium carbonate (4 g, 28.9 mmol) in acetone (20 mL) at 60° C. overnight. Cool to room temperature and pour into ethyl acetate (100 mL) and 5% aqueous ammonium chloride solution (100 mL). Separate the organic layer and wash it with water, saturated aqueous sodium chloride, dry (sodium sulfate), and concentrate to give the title compound and which is used directly in the next step without further purification.

Workup

  1. customSeparate the organic layer
  2. washwash it with water, saturated aqueous sodium chloride
  3. dry with materialdry (sodium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-a5f2bb1c9bab4c6394157c207f2e0ebb
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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