Hydrochloric Acid → 2-[2-Nitro-3-(2-fluorophenoxy)phenyl]acetic acid

HRID 2418383Notes

Reaction equation

HRID 2418383 reaction equation
[N+:1]([C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([O:21]CC)=[O:20])([O-:3])=[O:2].[OH-].[K+].O.Cl>CO>[N+:1]([C:4]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:18][C:19]([OH:21])=[O:20])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 20446203Ethyl 2-[2-nitro-3-(2-fluorophenoxy)phenyl]acetate

Product 1

HCID 204461882-[2-Nitro-3-(2-fluorophenoxy)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ethyl 2-[2-nitro-3-(2-fluorophenoxy)phenyl]acetate in methanol (50 ml) was added to a solution of potassium hydroxide (20 g) in methanol (50 ml) with stirring under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Water (700 ml) was added to the reaction mixture and the resultant aqueous solution was adjusted to pH 2.0 with conc. hydrochloric acid. The precipitating crystals were collected by filtration, washed with water and recrystallized from a mixture of ethyl acetate and n-hexane (1:1) to give 2-[2-nitro-3-(2-fluorophenoxy)phenyl]acetic acid (31.9 g). mp 144°-146° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. filtrationThe precipitating crystals were collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixture of ethyl acetate and n-hexane (1:1)

Sources & evidence

ORD record
ord-a2f645d2464e4b889105092f5db570dc
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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