Methyl iodide → 6-Methoxy-2-methyl-1-tetralone

HRID 643909Notes

Reaction equation

HRID 643909 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:14]I.[H-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH3:14])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 141126-Methoxy-alpha-tetraloneHCID 24758Sodium hydride

Product 1

HCID 111168446-Methoxy-2-methyl-1-tetralone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-methoxy-1-tetralone (5.0 g, 28.4 mmol), methyl iodide (20 mL, 262 mmol) and sodium hydride (60%, 5.5 g, 138 mmol, prewashed twice with hexanes) in toluene is heated at 80° C. for 3 days. The mixture is quenched carefully with water and is partitioned between EtOAc and brine. The organic extract is dried with MgSO4, concentrated and purified via column chromatography to give the title compound as a light yellow oil: 1H NMR (CDCl3) δ 1.27 (d, J=7 Hz, 3H), 1.83-1.89 (m, 1H), 2.10-2.15 (m, 1H), 2.51-2.60 (m, 1H), 2.90-3.00 (m, 2H), 3.85 (s, 3H), 6.68 (s, 1H), 6.81 (d, J=8.6 Hz, 1H), 8.01 (d, J=8.6 Hz, 1H).

Workup

  1. customThe mixture is quenched carefully with water
  2. customis partitioned between EtOAc and brine
  3. extractionThe organic extract
  4. dry with materialis dried with MgSO4
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-7da7ace0b2874a3096446efe91a1672e
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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