Hydrochloric Acid → HCID 54230354, compound

HRID 2419281Notes

Reaction equation

HRID 2419281 reaction equation
[OH:1]O.[F:3][C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[CH2:18][C:19](=[O:23])C(O)=O)=[CH:6][CH:5]=1.Cl>[OH-].[Na+]>[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[CH2:18][C:19]([OH:23])=[O:1])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 214270062-(4-Fluorophenoxy)-5-nitro-α-oxobenzenepropanoic acid

Product 1

HCID 54230354HCID 54230354, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

560 ml. of a 10% aqueous solution of hydrogen peroxide are added dropwise at 0° over a period of 75 minutes to a solution of 142 g. of 2-(4-fluoro-phenoxy)-5-nitro-phenylpyruvic acid in 2.23 liters of 10% sodium hydroxide solution cooled to 0° C. The mixture is subsequently stirred for 3 hours at 25° C. and then acidified with 500 ml. of concentrated hydrochloric acid with cooling. This mixture is extracted twice with methylene chloride. The methylene chloride solutions are washed with water, dried over sodium sulfate and concentrated in vacuo. The residue is crystallized from benzene/hexane, and there is obtained 2-(4-fluorophenoxy)-5-nitro-phenylacetic acid having a melting point of 129°-130° C.

Workup

  1. extractionThis mixture is extracted twice with methylene chloride
  2. washThe methylene chloride solutions are washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is crystallized from benzene/hexane

Sources & evidence

ORD record
ord-de40c4db02414739a5eb8fab7c9c9718
Source dataset
uspto-grants-1978_08
Patent number
US04105664

Reaction notes

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