Potassium Hydroxide → 1-(2-Methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylic acid

HRID 893193Notes

Reaction equation

HRID 893193 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13]([C:15]1([C:18]([O:20]CC)=[O:19])[CH2:17][CH2:16]1)=[O:14]>C(O)C.O>[CH3:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13]([C:15]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]1)=[O:14]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19096823Ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate

Product 1

HCID 190969061-(2-Methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution containing 0.34 gram (0.006 mole) of potassium hydroxide and 0.109 gram (0.006 mole) of water in 80 milliliters of ethanol was prepared in a 250 milliliter round bottom flask. With cooling to a temperature of 0° C. in an ice/NaCl bath and stirring, a solution of ethyl 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylate prepared in Example III in a small volume of ethanol was added and the mixture allowed to stir with warming to room temperature over a 72 hour period. The mixture was vacuum evaporated to give a white solid residue which was dissolved in water and extracted twice with ether. The ether extracts were discarded. The water solution was acidified to a pH of 2 with 25% Hcl solution causing separation of a solid which was taken up into ether, and the acidified aqueous phase was extracted four times. The combined ether extracts were dried over magnesium sulfate and vacuum evaporated to give a white solid. This white solid was water-washed and dried in a vacuum oven to give 1.85 grams (0.006 mole) of 1-(2-methyl-4,5-dichlorophenylaminocarbonyl)cyclopropanecarboxylic acid having a melting point of 248° C.-251° C.

Workup

  1. customwas prepared in a 250 milliliter round bottom flask
  2. stirringto stir
  3. temperaturewith warming to room temperature over a 72 hour period
  4. customevaporated
  5. customto give a white solid residue which
  6. extractionextracted twice with ether
  7. customseparation of a solid which
  8. extractionthe acidified aqueous phase was extracted four times
  9. dry with materialThe combined ether extracts were dried over magnesium sulfate and vacuum
  10. customevaporated
  11. customto give a white solid
  12. washwashed
  13. customdried in a vacuum oven

Sources & evidence

ORD record
ord-281d875acc04468ea039456c814a4280
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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