Hydrochloric Acid → 2-(4-Fluorophenoxy)-5-nitro-α-oxobenzenepropanoic acid

HRID 2419280Notes

Reaction equation

HRID 2419280 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH:9]=O)=[CH:4][CH:3]=1.[C:20](=[O:23])(O)[O-:21].[K+].[C:25](NCC(O)=O)(=[O:27])C.C(OC(=O)C)(=O)C.Cl>O.C(O)(=O)C>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:8]=2[CH2:9][C:25](=[O:27])[C:20]([OH:21])=[O:23])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 10972AcetylglycineHCID 516893Potassium BicarbonateHCID 22767921HCID 22767921, compound

Product 1

HCID 214270062-(4-Fluorophenoxy)-5-nitro-α-oxobenzenepropanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

183.4 G. of 2-(4-fluoro-phenoxy)-5-nitro-benzaldehyde are stirred at reflux for 20 minutes together with 71 g. of potassium bicarbonate and 82 g. of acetylglycine in 395 ml. of acetic anhydride. Then, there are added successively 1.62 liters of glacial acetic acid, 870 ml. of water and 675 ml. of concentrated hydrochloric acid, and the mixture is stirred for 5 hours at reflux. The resulting mixture is cooled and 1.2 liters of water are added. The mixture is extracted with 3.1 liters of methylene chloride in 3 portions. The methylene chloride solutions are washed twice with 2 liters of water each time and subsequently extracted with a solution of 250 g. of sodium carbonate in 4.5 liters of water. The obtained bicarbonate solutions are acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solutions are dried over sodium sulfate and evaporated in vacuo. The crystalline residue is boiled out with 400 ml. of benzene. The crystals are removed by filtration and there is obtained 2-(4-fluoro-phenoxy)-5-nitro-phenylpyruvic acid having a melting point of 142°-143° C. By concentration of the filtrate, there is obtained an additional amount of this compound.

Workup

  1. temperatureat reflux for 20 minutes together with 71 g
  2. temperatureat reflux
  3. temperatureThe resulting mixture is cooled
  4. extractionThe mixture is extracted with 3.1 liters of methylene chloride in 3 portions
  5. washThe methylene chloride solutions are washed twice with 2 liters of water each time
  6. extractionsubsequently extracted with a solution of 250 g
  7. extractionextracted with ethyl acetate
  8. dry with materialThe ethyl acetate solutions are dried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe crystals are removed by filtration

Sources & evidence

ORD record
ord-2117391398db43eeb8f1423ccdbbe269
Source dataset
uspto-grants-1978_08
Patent number
US04105664

Reaction notes

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