Sodium Hydroxide → 4-Benzyloxy-3-methylnaphthol

HRID 277631Notes

Reaction equation

HRID 277631 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([O:19]C(=O)C2C=CC=CC=2)=[CH:11][C:10]=1[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([OH:19])=[CH:11][C:10]=1[CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 226254021-Benzyloxy-2-methyl-4-benzoyloxynaphthalene

Product 1

HCID 120516524-Benzyloxy-3-methylnaphthol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.9 g (0.032 mol) of 1-benzyloxy-2-methyl-4-benzoyloxynaphthalene was suspended in 120 ml of methanol, and to this was added 20 ml of 2N NaOH, followed by stirring for 2 hours at room temperature. After evaporation of methanol from the reaction mixture under reduced pressure, the residue was acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a sodium hydrogen carbonate aqueous solution and then with water, and ethyl acetate evaporated under reduced pressure. The residue was dissolved in methanol, decolorized with activated carbon, and following filtering out of the activated carbon, water was added to the filtrate, and precipitated crystals were collected, recrystallized from methanol-water to give 5.2 g of white plates, m.p. 159-161° C.

Workup

  1. customAfter evaporation of methanol from the reaction mixture under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a sodium hydrogen carbonate aqueous solution
  4. customwith water, and ethyl acetate evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol
  6. filtrationfollowing filtering out of the activated carbon, water
  7. additionwas added to the filtrate
  8. customprecipitated crystals
  9. customwere collected
  10. customrecrystallized from methanol-water
  11. customto give 5.2 g of white plates, m.p. 159-161° C.

Sources & evidence

ORD record
ord-17da96710acd4c2b918410798d3600c0
Source dataset
uspto-grants-2002_03
Patent number
US06358515B2

Reaction notes

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