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

HRID 900284Notes

Reaction equation

HRID 900284 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-eeba3e5afea649b18ac13c3ca0a15dfe
Source dataset
uspto-grants-2008_04
Patent number
US07358257B2

Reaction notes

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