Potassium Carbonate → HCID 68816406, compound

HRID 1436649Notes

Reaction equation

HRID 1436649 reaction equation
C[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.C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH2:24][CH3:25].[OH-].[Na+]>CN(C=O)C.CO>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH2:23][CH2:24][CH3:25])[CH:13]=[C:4]([C:3]([OH:2])=[O:15])[CH:5]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 68816406HCID 68816406, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Heat commercially available 5-hydroxy-isophthalic acid dimethyl ester (1.0 g, 4.8 mmol), potassium carbonate (5.25 g, 38 mmol) and iodopropane (1.36 g, 8.0 mmol) in DMF (20 mL) at 70° C. for 8 h. Cool to room temperature, partition between ethyl acetate and 10% aqueous potassium carbonate. Wash the ethyl acetate layer with 1 N lithium chloride, saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate. Dissolve the residue in acetone (10 mL) and add a solution of NaOH (192 mg, 4.80 mmol) in methanol (2 mL). Stir at room temperature 16 h and concentrate. Partition between diethyl ether and 0.1 N citric acid, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. custompartition between ethyl acetate and 10% aqueous potassium carbonate
  2. washWash the ethyl acetate layer with 1 N lithium chloride, saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. dissolutionDissolve the residue in acetone (10 mL)
  6. concentrationconcentrate
  7. customPartition between diethyl ether and 0.1 N citric acid
  8. dry with materialdry (magnesium sulfate)
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-bba55b7534894d598dff76d2455f10b2
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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