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

HRID 1071739Notes

Reaction equation

HRID 1071739 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-74d5456f163b4d09910721f4d2d18c9e
Source dataset
uspto-grants-2005_06
Patent number
US06906063B2

Reaction notes

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