Hydrochloric Acid → 4-hydroxy-1,1-dimethyl-2(1H)-naphthalenone

HRID 494467Notes

Reaction equation

HRID 494467 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[C:4](=[O:14])[C:3]=1C(OCC)=O.Cl>O1CCOCC1.C(OCC)(=O)C.O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:12])([CH3:13])[C:4](=[O:14])[CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57604805Ethyl 1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydro-2-naphthalenecarboxylate

Product 1

HCID 123691024-hydroxy-1,1-dimethyl-2(1H)-naphthalenone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 9E (2.25 g, 8.65 mmol) in dioxane (50 mL) was treated with 1 N HCl solution (60 mL) and the mixture was stirred at reflux for 6 hours, cooled to 25° C., diluted with ethyl acetate and water. The organic layer was washed with water (2×) and saturated sodium chloride solution (1×), dried(Na2SO4), filtered and concentrated in vacuo. The residue was triturated with ether and filtered.

Workup

  1. temperatureat reflux for 6 hours
  2. washThe organic layer was washed with water (2×) and saturated sodium chloride solution (1×), dried(Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e132b16ef53f422793d779137ae29935
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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