Methyl iodide → 2-Decyl-6-methoxynaphthalene

HRID 1476361Notes

Reaction equation

HRID 1476361 reaction equation
[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([OH:21])[CH:15]=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:22]1COCC1.[H-].[Na+].CI>O>[CH2:1]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[CH:14]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 21746791HCID 21746791, compound

Product 1

HCID 867043812-Decyl-6-methoxynaphthaleneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, 6-n-decyl-2-hydroxynaphthalene (5.68 g, 20 mmol) and a THF (200 ml) solution of 55% NaH (oil dispersion, 880 mg, 20 mmol) were stirred at room temperature for 40 minutes. CH3I (1.48 ml, 24 mmol) was added to the mixed solution, and the mixed solution was heated under reflux for 12 hours. Water (20 ml) was added to the mixture at 0° C., and the mixture was washed with saline water. Organic layers were combined, and dried with MgSO4, and condensed with an evaporator. The condensed solution was recrystallized from methanol to obtain 6-n-decyl-2-methoxynaphthalene (compound (3)-64) (5.0 g, 85%) as a white solid.

Workup

  1. temperaturethe mixed solution was heated
  2. temperatureunder reflux for 12 hours
  3. washthe mixture was washed with saline water
  4. dry with materialdried with MgSO4, and condensed with an evaporator
  5. customThe condensed solution was recrystallized from methanol

Sources & evidence

ORD record
ord-3361c7cdb7b04f5dab4e51def401d78c
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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