4-Methoxy-1-naphthol → 4,4-dimethoxy-4H-naphthalen-1-one

HRID 969596Notes

Reaction equation

HRID 969596 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.[C:14](O)(=[O:16])C.C(O)(=O)C.IC1C=CC=CC=1.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3]1([O:16][CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 665424-Methoxy-1-naphtholHCID 516892Sodium BicarbonateHCID 12217721Iodo benzene diacetate

Product 1

HCID 110957174,4-dimethoxy-4H-naphthalen-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

For example, a solution of 4-methoxynaphthol (16 mmol) and iodobenzene diacetate (6.1 g, 19 mmol) in methanol (75 mL) is stirred at room temperature, under a nitrogen atmosphere for 1 hour. The resultant dark blue solution is poured into a saturated solution of NaHCO3 (75 mL), then evaporated to reduced volume. The blue oil is extracted with CH2Cl2 (3×75 mL) and the organic layer is washed with water (3×75 mL), brine (2×75 mL), and is dried over MgSO4, and filtered and evaporated to dryness (bath temp. <40° C.) to yield the product as a dark blue semi-solid.

Workup

  1. customis stirred at room temperature, under a nitrogen atmosphere for 1 hour
  2. customevaporated to reduced volume
  3. extractionThe blue oil is extracted with CH2Cl2 (3×75 mL)
  4. washthe organic layer is washed with water (3×75 mL), brine (2×75 mL)
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness (bath temp. <40° C.)

Sources & evidence

ORD record
ord-36111f2eb15c49d19f9ff180681d94e6
Source dataset
uspto-grants-2007_12
Patent number
US07307099B2

Reaction notes

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