Methyl iodide → 2-Methoxy-1,4-dipropylbenzene

HRID 1816400Notes

Reaction equation

HRID 1816400 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH3:12])=[CH:6][C:5]=1[OH:13])[CH2:2][CH3:3].I[CH3:15].[H-].[Na+]>CN(C=O)C>[CH3:15][O:13][C:5]1[CH:6]=[C:7]([CH2:10][CH2:11][CH3:12])[CH:8]=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 224937272,5-Dipropylphenol

Product 1

HCID 224937172-Methoxy-1,4-dipropylbenzeneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,5-dipropylphenol (3.50 g, 19.6 mmol) and iodomethane (3.70 mL, 58.8 mmol) in DMF (65 mL) at 0° C. was added sodium hydride (1.60 g, 39.2 mmol, 60% dispersion in oil) in two portions. The resulting mixture was stirred at 0° C. for 10 min and then at room temperature for 14 h. After being quenched with water, the mixture was extracted in hexanes (3×100 mL) with 50% saturated brine (50 mL). Flash chromatography with silica gel (100% hexanes) afforded the title compound as a colorless liquid (3.70 g, 97% yield): 1H NMR (300 MHz, CDCl3) δ 0.95 (two overlapping triplets, 6H), 1.60 (m, 4H), 2.55 (m, 4H), 3.81 (s, 3H), 6.66 (s, 1H), 6.70 (d, 1H, J=7.5 Hz), 7.02 (d, 1H, J=7.5 Hz).

Workup

  1. waitat room temperature for 14 h
  2. customAfter being quenched with water
  3. extractionthe mixture was extracted in hexanes (3×100 mL) with 50% saturated brine (50 mL)

Sources & evidence

ORD record
ord-f8e1b65d510f4db8a367456aeba53cd2
Source dataset
uspto-grants-2005_04
Patent number
US06884814B2

Reaction notes

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