Potassium Carbonate → Methyl 2-(5-chloro-2-formylphenoxy)propionate

HRID 1488393Notes

Reaction equation

HRID 1488393 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5](=[CH:8][CH:9]=1)[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH:3]=1)[O:10][CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 5201014-Chloro-2-hydroxybenzaldehyde

Product 1

HCID 53800060Methyl 2-(5-chloro-2-formylphenoxy)propionateYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 22.0 g (0.141 mole) of 4-chlorosalicylaldehyde, 30 g (0.22 mole) of anhydrous potassium carbonate, and 30.0 g (0.184 mole) of methyl 2-bromopropionate in 120 mL of N,N-dimethylformamide was heated at 80° C. for approximately 17 hours. At the end of that period, the reaction mixture was poured over ice and extracted successively with diethyl ether and ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate, and filtered. The solvents were then evaporated under reduced pressure, leaving a residue weighing 20 g. This residue was purified by placing it on a silica gel column and eluting with diethyl ether/petroleum ether (25/75). After the product-containing fractions were combined and the solvents evaporated under reduced pressure, 6.23 g of methyl 2-(5-chloro-2-formylphenoxy)propionate was isolated as a yellow liquid. Similarly, other fractions were combined and evaporated, yielding 1.69 g of methyl 2-(3-chloro-2-formylphenoxy)propionate as a yellow liquid. The NMR spectra of both compounds were consistent with proposed structure of each. This reaction was repeated several times.

Workup

  1. additionAt the end of that period, the reaction mixture was poured over ice
  2. extractionextracted successively with diethyl ether and ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvents were then evaporated under reduced pressure
  7. customleaving a residue
  8. customThis residue was purified
  9. washeluting with diethyl ether/petroleum ether (25/75)
  10. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-ab57be8b7c424e8a878abc5a165edee9
Source dataset
uspto-grants-1997_10
Patent number
US05674810

Reaction notes

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