Water → 2-(4-Chloro-2-formyl-phenoxy)-pentanoic acid ethyl ester

HRID 658926Notes

Reaction equation

HRID 658926 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([O:13][C:14](=[O:20])[CH:15](Br)[CH2:16][CH2:17][CH3:18])[CH3:12].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH2:11]([O:13][C:14](=[O:20])[CH:15]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH2:16][CH2:17][CH3:18])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 79071Ethyl 2-bromovalerate

Product 1

HCID 594280852-(4-Chloro-2-formyl-phenoxy)-pentanoic acid ethyl esterYield 84.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-chloro-2-hydroxy-benzaldehyde (15 g, 0.1 mol), 2-bromo-pentanoic acid ethyl ester (27 g, 0.13 mol) and K2CO3 (27 g, 0.2 mol) in DMF (100 mL) was heated at 140° C. for 1 h. After cooled to room temperature, the mixture was poured into water and the aqueous phase was extrated with EtOAc thrice. The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column to give the title compound as a colorless oil (24 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-4cb03f3b83104bf58b09015ff07d56e9
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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