Methyl iodide → 5-Methoxy-1,2,3,4-tetrahydronaphthalene

HRID 1719197Notes

Reaction equation

HRID 1719197 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CI.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:11][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 2211715-Methoxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5,6,7,8-Tetrahydro-1-naphthol (9.85 g, 66mM), methyl iodide (30.6 g, 215mM) and potassium carbonate (15 g, 90.8mM) in acetone (500 ml) were heated under reflux with stirring for 3 days. The mixture was evaporated and the residue was extracted with 2M sodium hydroxide and ether. The organic layer was washed and dried to give 1-methoxy-5,6,7,8-tetrahydronaphthalene as as oil.

Workup

  1. temperatureunder reflux
  2. customThe mixture was evaporated
  3. extractionthe residue was extracted with 2M sodium hydroxide and ether
  4. washThe organic layer was washed
  5. customdried

Sources & evidence

ORD record
ord-9ab89f5c1a154a34a41fb6f5e5631fd1
Source dataset
uspto-grants-1985_09
Patent number
US04539319

Reaction notes

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