Potassium Carbonate → 3-(4-Chloro-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

HRID 504475Notes

Reaction equation

HRID 504475 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

Product 1

HCID 575660603-(4-Chloro-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl esterYield 923.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-chloro-2-hydroxy-benzaldehyde (3.1 g, 2 mmol), 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (5.46 g, 24 mmol), K2CO3 (5.5 g, 40 mmol) and KI (0.1 g) were mixed in DMF (20 mL). Then the mixture was irradiated by microwave for an hour at 150° C. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was dried over anhydrous Na2SO4 and concentrated to give title compound (Yield: 5 g, 92.5%).

Workup

  1. customThen the mixture was irradiated by microwave for an hour at 150° C
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N NaOH
  6. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fd15740c394e48e793191144947b8f96
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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