Hydrochloric Acid → 4-Hydroxy-2-methyl-1-naphthyl acetate

HRID 1787145Notes

Reaction equation

HRID 1787145 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15]C(=O)C)=[CH:7][C:6]=1[CH3:19])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[CH:7][C:6]=1[CH3:19])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11310AcetomenaphthoneHCID 11430Potassium Carbonate

Product 1

HCID 3131344-Hydroxy-2-methyl-1-naphthyl acetateYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(acetyloxy)-2-methyl-1-naphthyl acetate (25 g, 96.8 mmol) in methanol (300 mL) was added potassium carbonate (58.1 g, 420 mmol), and the mixture was stirred under argon atmosphere at room temperature for 15 minutes. Water was poured into the mixture, which was neutralized with hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated brine and dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 21 g (yield: quantitative) of the title compound. Oily matter.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-163546329c8d4d4eb6023eb903dae6b2
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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