(4-chloro-2-Methylphenoxy)acetic acid → 1,2-Dimethyl-3,5-diphenylpyrazolium 4-chloro-2-methylphenoxyacetate

HRID 426559

Reaction equation

HRID 426559 reaction equation
[OH-].[CH3:2][N+:3]1[N:4]([CH3:20])[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[C:24]([CH3:33])[CH:23]=1>O>[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([O-:30])=[O:29])=[C:24]([CH3:33])[CH:23]=1.[CH3:20][N+:4]1[N:3]([CH3:2])[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7204(4-chloro-2-Methylphenoxy)acetic acid2×HCID 128736641,2-Dimethyl-3,5-diphenylpyrazolium hydroxide

Product 1

HCID 203903421,2-Dimethyl-3,5-diphenylpyrazolium 4-chloro-2-methylphenoxyacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2-Dimethyl-3,5-diphenylpyrazolium hydroxide in a H2O solution was titrated with 4-chloro-2-methylphenoxyacetic acid (MCPA), a known herbicide until pH 7 was obtained and retained for 48 hours. MCPA was added as a solid and slowly dissolved. ##STR7## The H2O solution was evaporated to a low volume (oil) and toluene/acetone azeotroped several times. Hexane (5% acetone) was added and the oil solidified to a light yellow solid and was filtered, washed with hexane and dried. 6.5 Grams, melting point 138° C. to 140° C. of a light yellow solid was obtained.

Workup

  1. customa known herbicide until pH 7 was obtained
  2. dissolutionslowly dissolved
  3. custom##STR7## The H2O solution was evaporated to a low volume (oil) and toluene/acetone azeotroped several times
  4. additionHexane (5% acetone) was added
  5. filtrationwas filtered
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-8aa8394104a34b45a23a594a7d7ea0d3
Source dataset
uspto-grants-1979_10
Patent number
US04170464

Linked notes

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