P-Cresol → 3-(4-methylphenoxy)nitrobenzene

HRID 392955Notes

Reaction equation

HRID 392955 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+]([O-])=O)[CH:13]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:14]2[CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:17]=[CH:16][CH:15]=2)=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 74521,3-DinitrobenzeneHCID 10796Cesium carbonate

Product 1

HCID 111280783-(4-methylphenoxy)nitrobenzeneYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of p-cresol (5.76 g, 0.053 mol) and 1,3-dinitrobenzene (8.97 g, 0.053 mol) in 100 mL of dimethylsulfoxide was added cesium carbonate (43.4 g, 0.133 mol). The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature, quenched with water, and extracted with diethyl ether. The organic layers were combined, washed with 0.1 N HC1 and water, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 1:4 ethyl acetate in hexane to afford 8.0 g (66%) of the desired 3-(4-methylphenoxy)nitrobenzene product as a yellow oil. 1H NMR (CDCl3) δ 7.83 (s, 1H), 7.64 (t, 1H), 7.32 (d, 1H), 7.18 (d, 1H), 7.09 (d, 2H), 6.8 (d, 2H), 2.20 (s, 1H).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with water
  3. extractionextracted with diethyl ether
  4. washwashed with 0.1 N HC1 and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel eluting with 1:4 ethyl acetate in hexane

Sources & evidence

ORD record
ord-3ef71774566a4b57ac234aa72b76196f
Source dataset
uspto-grants-2004_10
Patent number
US06803388B2

Reaction notes

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