3-Methyl-1-naphthyl acetate → 1-Naphthol, 3-methyl-

HRID 1589730Notes

Reaction equation

HRID 1589730 reaction equation
C([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([CH3:15])[CH:6]=1)(=O)C>[OH-].[K+]>[CH3:15][C:7]1[CH:6]=[C:5]([OH:4])[C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

3

Reactant 1

HCID 137648093-Methyl-1-naphthyl acetate

Product 1

HCID 261351-Naphthol, 3-methyl-Yield 27.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Crude 1-acetoxy-3-methylnaphthalene (84 g, 0.42 mole) was boiled with 10% ethanolic potassium hydroxide (300 cm3) for 3 hours. Ethanol was distilled off and the residue dissolved in water and extracted with toluene to remove neutral products. The aqueous alkaline solution was carefully acidified with dilute hydrochloric acid and the liberated 3-methyl-l-naphthol extracted with ether. The ether extract was washed with water, dried and filtered. Ether solvent was removed leaving 3-methyl-l-naphthol (18.4 g) as clear colorless crystals.

Workup

  1. distillationEthanol was distilled off
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with toluene
  4. customto remove neutral products
  5. extractionthe liberated 3-methyl-l-naphthol extracted with ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. customdried
  9. filtrationfiltered
  10. customEther solvent was removed

Sources & evidence

ORD record
ord-12990e0e8b8d420b9995ac40ed251615
Source dataset
uspto-grants-1993_04
Patent number
US05200116

Reaction notes

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