2-Chloro-5-methylphenol → 1-Chloro-2-methoxy-4-methylbenzene

HRID 1874757Notes

Reaction equation

HRID 1874757 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[CH3:10][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO>[CH3:10][O:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 120082-Chloro-5-methylphenolHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzeneYield 55%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-Chloro-5-methylphenol (5.0 g, 35.0 mmol) was dissolved in 50% CH2Cl2/methanol (100 mL) and trimethylsilyl diazomethane (2.0 M in hexanes, 25 mL) was added dropwise until a persistent yellow color was observed. The solution was stirred overnight. The solvent was evaporated and the crude product was purified by column chromatography (hexane/EtOAc) to afford the title compound (3.0 g, 55%) as an oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.25 (d, 1H), 6.95 (d, 1H), 6.74 (dt, 1H), 3.81 (s, 3H), 2.28 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-baaf6a27d0f0460a8426ffd1809e2de0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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