Water → HCID 15480472, compound

HRID 557198Notes

Reaction equation

HRID 557198 reaction equation
O.CO[CH:4](OC)[CH2:5][O:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[CH3:16]>ClC1C=CC=CC=1>[CH3:16][C:8]1[C:7]2[O:6][CH:5]=[CH:4][C:12]=2[C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 962WaterHCID 17985754HCID 17985754, compound

Product 1

HCID 15480472HCID 15480472, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

Add Amberlyst® 15 ion-exchange resin (36 g) to chlorobenzene (700 mL). Heat the reaction mixture to reflux and azeotrope out water, to dry the resin. Dissolve 2-(2,2-dimethoxyethoxy)-1-methyl-4-nitrobenzene (34.8 g, 144 mmol) in chlorobenzene (125 mL) and add dropwise to the stirring, refluxing reaction mixture under nitrogen over 15 minutes. Continue refluxing for 1.5 hours. Cool to room temperature, filter to remove the resin and concentrate under reduced pressure. Dissolve the residue in hexane, diethyl ether (1:1), wash with 0.5 M aqueous sodium hydroxide, aqueous saturated sodium chloride, dry the organic phase over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Chromatograph on flash silica using hexane, ethyl acetate (9:1) and recrystallize from hexane, toluene (1:1) to obtain the desired compound as a yellow solid (9.7 g, 42%).

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureto reflux
  3. customto dry the resin
  4. temperaturerefluxing
  5. customreaction mixture under nitrogen over 15 minutes
  6. temperatureContinue refluxing for 1.5 hours
  7. filtrationfilter
  8. customto remove the resin
  9. concentrationconcentrate under reduced pressure
  10. dissolutionDissolve the residue in hexane
  11. washdiethyl ether (1:1), wash with 0.5 M aqueous sodium hydroxide, aqueous saturated sodium chloride
  12. dry with materialdry the organic phase over anhydrous magnesium sulfate
  13. filtrationfilter
  14. concentrationconcentrate under reduced pressure
  15. customrecrystallize from hexane, toluene (1:1)

Sources & evidence

ORD record
ord-c2ca3328070e482dbbc7cd073ae99a44
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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