Chloroacetic Acid → 2-Naphthoxyacetic acid

HRID 847237Notes

Reaction equation

HRID 847237 reaction equation
[OH-].[K+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:13].Cl[CH2:15][C:16]([OH:18])=[O:17]>O>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 86632-NaphtholHCID 14797Potassium Hydroxide

Product 1

HCID 84222-Naphthoxyacetic acidYield 14.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of potassium hydroxide (10.0 g, 0.175 mol) in H2O (100 mL) was added 2-naphthol (10.43 g, 72 mmol), followed by 2-chloroacetic acid (7.79 g, 83 mmol). The resulting mixture was heated at 70° C. for 4 h, then allowed to cool. The mixture was filtered, and the filtrate was extracted with EtOAc. The aqueous phase was made acidic by the addition of 3N HCl and extracted with EtOAc. The organic phase from the acidic extraction was washed successively with H2O and saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (2.11 g, 14%).

Workup

  1. temperatureto cool
  2. filtrationThe mixture was filtered
  3. extractionthe filtrate was extracted with EtOAc
  4. additionThe aqueous phase was made acidic by the addition of 3N HCl
  5. extractionextracted with EtOAc
  6. extractionThe organic phase from the acidic extraction
  7. washwas washed successively with H2O and saturated aqueous NaCl
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-62dc88ba17a640449d3772db0424ad2d
Source dataset
uspto-grants-1992_08
Patent number
US05140047

Reaction notes

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