Ethyl Acetate → 4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

HRID 1609714Notes

Reaction equation

HRID 1609714 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[CH:13]([C:16]1[CH:17]=[C:18]([OH:24])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[CH3:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[C:7]([CH3:8])[C:2]=1[O:24][C:18]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:16]([CH:13]([CH3:15])[CH3:14])[CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzeneHCID 113326753-Isopropyl-4-methoxyphenol

Product 1

HCID 103136024-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Chloro-3,5-dimethylnitrobenzene (2.12 g), 1.9 g of 3-isopropyl-4-methoxyphenol, and 1.74 g of potassium carbonate are heated 18 hrs at 125° in 25 ml dimethylsulfoxide. The mixture is poured into ethyl acetate and extracted once with water and five times with brine. The ethyl acetate is dried, filtered, and stripped to yield an oil which is chromatographed on silica gel with 97:3 hexane:ethyl acetate to afford 3,5-dimethyl-4-(3'-isopropyl-4'-methoxyphenoxy)-nitro benzene NMR (CDCl3): δ1.1 (6H,d), 2.2 (6H,s), 3.3 (1H,m), 3.7 (3H, s) 6.3 (1H,d of d), 6.6 (1H,d), 6.7 (1H, d), 8.0 (2H, s).

Workup

  1. extractionextracted once with water and five times with brine
  2. dry with materialThe ethyl acetate is dried
  3. filtrationfiltered
  4. customto yield an oil which
  5. customis chromatographed on silica gel with 97:3 hexane

Sources & evidence

ORD record
ord-de2bea3959aa4dfd859bc38db9b2b1fc
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

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