Methyl iodide → 1-Chloro-2-methoxy-4-methylbenzene

HRID 1437556Notes

Reaction equation

HRID 1437556 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120082-Chloro-5-methylphenol

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzeneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-methylphenol (10.7 g, 75 mmol) in DMF (40 mL) was added potassium carbonate (26 g, 188 mmol) followed by neat methyl iodide (4.9 mL, 79 mmol). The reaction mixture was stirred at room temp for 6 hr, extracted with EtOAc, washed with water and brine, dried and concentrated in vacuo to give 4-chloro-3-methoxytoluene (10.8 g, 92%). 1H-NMR (DMSO-d6): δ 2.26 (s, 3H), 3.79 (s, 3H), 6.71-6.73 (dd, 1H), 6.94 (s, 1H), 7.22-7.24 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24f25a1c464f4ac491ec64db37f4ee61
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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