Hydrochloric Acid → (3,5-Dichloro-6-fluoro-2-pyridyloxy) acetic acid

HRID 1448406Notes

Reaction equation

HRID 1448406 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[C:9]([F:15])[N:8]=1)C.C(O)C.[OH-].[Na+].Cl>O>[Cl:13][C:12]1[C:7]([O:6][CH2:5][C:4]([OH:16])=[O:3])=[N:8][C:9]([F:15])=[C:10]([Cl:14])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 21522711Ethyl [(3,5-dichloro-6-fluoropyridin-2-yl)oxy]acetate

Product 1

HCID 20379575(3,5-Dichloro-6-fluoro-2-pyridyloxy) acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17 grams (0.06 mole) of ethyl-(3,5-dichloro-6-fluoro-2-pyridyloxy)acetate in 90 milliliters of commercial grade ethanol and 2.8 grams of sodium hydroxide in 25 milliliters of water was refluxed for ~20 minutes. Thereafter 5.9 cubic centimeters of concentrated hydrochloric acid was added thereto and the mixture stirred and cooled for 15 minutes. The mixture was filtered to recover the solid which precipitated and the solid was extracted exhaustively with boiling hexane followed by extraction with a hexane-benzene mixture. After drying, the (3,5-dichloro-6fluoro-2-pyridyloxy) acetic acid product was recrystallized from hexane and was recovered in a yield of ~6 grams and melted at 140°-144° C. Upon analysis, the product was found to have carbon, hydrogen, chlorine and nitrogen contents of 36.04, 2.11, 29.28 and 5.64 percent, respectively, as compared with the theoretical contents of 35.03, 1.67, 29.54 and 5.83 percent, respectively, calculated for the above-named compound.

Workup

  1. temperaturewas refluxed for ~20 minutes
  2. temperaturecooled for 15 minutes
  3. filtrationThe mixture was filtered
  4. customto recover the solid which
  5. customprecipitated
  6. extractionthe solid was extracted exhaustively with boiling hexane
  7. extractionfollowed by extraction with a hexane-benzene mixture
  8. customAfter drying
  9. customthe (3,5-dichloro-6fluoro-2-pyridyloxy) acetic acid product was recrystallized from hexane
  10. customwas recovered in a yield of ~6 grams and melted at 140°-144° C

Sources & evidence

ORD record
ord-5e83fd4075fb4a71a685cc5c3fac85d2
Source dataset
uspto-grants-1979_12
Patent number
US04180395

Reaction notes

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