Chloroacetic Acid → Naphthoxyacetic acid

HRID 847234Notes

Reaction equation

HRID 847234 reaction equation
[OH-].[K+].[C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl[CH2:15][C:16]([OH:18])=[O:17]>O>[C:3]1([O:13][CH2:15][C:16]([OH:18])=[O:17])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 70051-NaphtholHCID 14797Potassium Hydroxide

Product 1

HCID 76313Naphthoxyacetic acidYield 64.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of potassium hydroxide (2.98 g, 52.1 mmol) in H2O (35 mL) was added 1-naphthol (3.08 g, 21.4 mmol), followed by 2-chloroacetic acid (2.32 g, 24.7 mmol). The resulting mixture was heated at reflux for 3 h, then allowed to cool and 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 with saturated aqueous NaCl. The solvent was removed in vacuo to provide the title compound (2.78 g, 64%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. extractionextracted with EtOAc
  5. additionThe aqueous phase was made acidic by the addition of 3N HCl
  6. extractionextracted with EtOAc
  7. extractionThe organic phase from the acidic extraction
  8. washwas washed with saturated aqueous NaCl
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-325af5744be44a3692058cbf43447635
Source dataset
uspto-grants-1992_08
Patent number
US05140047

Reaction notes

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