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

HRID 504581Notes

Reaction equation

HRID 504581 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>[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

6

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 1

HCID 6228DimethylformamideSolvent

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 water phase was extracted with EtOAc thrice. The combined organic layers 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. extractionthe water phase was extracted with EtOAc thrice
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-9ae9a849bf7f48cf885ce71af35a19fe
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

Loading…