4-Chlorobenzoic Acid → HCID 21290692, compound

HRID 623210Notes

Reaction equation

HRID 623210 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[CH:18]([C:24]([CH3:26])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:18]([C:24](=[O:25])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 10340Sodium CarbonateHCID 11858Ethyl 2-chloroacetoacetate

Product 1

HCID 21290692HCID 21290692, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A solution of 15.65 g (0.1 mol) of 4-chlorobenzoic acid in 20 ml of dimethylformamide was added dropwise to a stirred suspension of 5.3 g (0.05 mol) of anhydrous sodium carbonate in 80 ml of dimethylformamide. The suspension was heated at 80° C. for 1 hour and a solution of 16.46 g (0.1 mol) of ethyl 2-chloroacetoacetate in 10 ml of dimethylformamide was added. The suspension was heated at 80° C. for 6 hours and left to cool overnight. The solvent was removed by evaporation under reduced pressure and the residue was partitioned between 400 ml of water and 300 ml of diethyl ether. The organic phase was separated and washed twice with 300 ml of water. The organic phase was dried over magnesium sulphate, filtered and the solvent was removed by evaporation under reduced pressure to yield 26.86 g (94%) of ethyl 2-(4-chlorobenzoyloxy)-3-oxo-butyrate in the form of an oil which was homogeneous according to thin-layer chromatography.

Workup

  1. temperatureThe suspension was heated at 80° C. for 6 hours
  2. waitleft
  3. temperatureto cool overnight
  4. customThe solvent was removed by evaporation under reduced pressure
  5. customthe residue was partitioned between 400 ml of water and 300 ml of diethyl ether
  6. customThe organic phase was separated
  7. washwashed twice with 300 ml of water
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-ed9042aceca94cdb9f899eb421cc1761
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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