Potassium Carbonate → HCID 57428728, compound

HRID 270126Notes

Reaction equation

HRID 270126 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[Cl:11][C:12]1[C:13]([OH:23])=[CH:14][C:15]([OH:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:11][C:12]1[C:13]([O:23][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)=[CH:14][C:15]([OH:22])=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 105751Benzoic acid, 5-chloro-2,4-dihydroxy-, methyl ester

Product 1

HCID 57428728HCID 57428728, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(chloromethyl)-4-methoxybenzene (1.53 g, 9.8 mmol), methyl 5-chloro-2,4-dihydroxybenzoate (1.98 g, 9.8 mmol) and potassiumcarbonate (1.35 g, 9.8 mmol) in acetone (15 mL) was stirred at reflux overnight. The mixture was filtered, solvent was removed in vacuo, the residue was dissolved in ethyl acetate and was washed with brine two times. The organic layer was dried over sodium sulphate, solvent was removed in vacuo and the residue was purified by recrystillaziation from methanol. (1.46 g, 46%) of the title compound was obtained.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe mixture was filtered
  3. customsolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwas washed with brine two times
  6. dry with materialThe organic layer was dried over sodium sulphate, solvent
  7. customwas removed in vacuo
  8. customthe residue was purified by recrystillaziation from methanol

Sources & evidence

ORD record
ord-e550dedff9c94e0994e39ea2f1730c81
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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