Potassium Carbonate → 2-(3-Isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile

HRID 636714Notes

Reaction equation

HRID 636714 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([OH:12])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2].Cl[C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=1[C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[CH:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[O:12][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=1[C:24]#[N:25])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113326753-Isopropyl-4-methoxyphenolHCID 212556544-Chloro-3-cyano-5-methylnitrobenzene

Product 1

HCID 155236442-(3-Isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrileYield 90.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 3-isopropyl-4-methoxyphenol (200 mg), 4-chloro-3-cyano-5-methylnitrobenzene (200 mg) and potassium carbonate (211 mg) in methylethylketone (8 mL) was refluxed for 18 h. The dark mixture was concentrated in vacuo, partitioned between ethyl acetate/water, the organic layer washed with about 2N sodium hydroxide, brine, dried over sodium sulfate and concentrated to a dark oil. Flash chromatography (10% ethyl acetate/hexanes) afforded 2-(3-isopropyl-4-methoxy-phenoxy)-3-methyl-5-nitrobenzonitrile as a yellow oil (300 mg).

Workup

  1. temperaturewas refluxed for 18 h
  2. concentrationThe dark mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate/water
  4. washthe organic layer washed with about 2N sodium hydroxide, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a dark oil

Sources & evidence

ORD record
ord-e6bb69dfbc2c4c959a14e11f822e4491
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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