Water → 2-Decanoyl-6-methoxynaphthalene

HRID 1476359Notes

Reaction equation

HRID 1476359 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>[N+](C)([O-])=O>[C:17]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 71192-MethoxynaphthaleneHCID 66982Decanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 867043802-Decanoyl-6-methoxynaphthaleneYield 82%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Under a nitrogen atmosphere, 2-methoxynaphthalene (64 g, 0.41 mol) easily available from a reagent manufacturer was dissolved in nitromethane (150 ml) dried with a molecular sieve 3A. Under an ice bath, aluminum chloride (80 g, 0.60 mol) was added. Subsequently, decanoyl chloride (92 ml, 0.45 mol) was dropped into the solution under the ice bath. The solution was stirred under room temperature for 5 hours, and water (100 ml) was dropped into the solution under the ice bath. The reaction solution was extracted with methylene chloride (200 ml×4), and the obtained organic layer was washed with water (100 ml×3). The organic layer was dried with anhydrous magnesium sulfate, and filtered. Then, the solvent was distilled away under reduced pressure. The obtained yellow solid was recrystallized from hexane to obtain 2-decanoyl-6-methoxynaphthalene (102 g, 82%) as a white solid.

Workup

  1. dry with materialdried with a molecular sieve 3A
  2. extractionThe reaction solution was extracted with methylene chloride (200 ml×4)
  3. washthe obtained organic layer was washed with water (100 ml×3)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled away under reduced pressure
  7. customThe obtained yellow solid was recrystallized from hexane

Sources & evidence

ORD record
ord-2924c8d48ab646c88424f38c7d274ffd
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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