Potassium Carbonate → 2-(4-Chloro-2-formyl-phenoxy)-butyric acid methyl ester

HRID 658909Notes

Reaction equation

HRID 658909 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:18])[CH:14](Br)[CH2:15][CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:18])[CH:14]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 95577Butanoic acid, 2-bromo-, methyl ester

Product 1

HCID 594280922-(4-Chloro-2-formyl-phenoxy)-butyric acid methyl esterYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-2-hydroxy-benzaldehyde (156 g, 1 mol), 2-bromo-butyric acid methyl ester (271 g, 1.5 mol), KI (2 g, 0.012 mol) and K2CO3 (276 g, 2 mol) in DMF (500 mL) was heated at 130° C. for 2 h. After cooled to room temperature, the mixture was concentrated. The residue was partitioned between EtOAc and water. The organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the title compound (240 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-38c640ed5c84425e88362a33bfd633bd
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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