Water → HCID 15480472, compound

HRID 751493Notes

Reaction equation

HRID 751493 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 38%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

Add Amberlyst® 15 ion-exchange resin (36 g) to chlorobenzene (700 mL), and heat the 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 this mixture dropwise to the stirring, refluxing reaction mixture under nitrogen over a 15 minute period. Continue refluxing for 1.5 hours, then cool to room temperature. Filter to remove the resin and concentrate under reduced pressure. Dissolve the residue in hexane and diethyl ether (1:1), then wash with 0.5M aqueous sodium hydroxide and aqueous saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Chromatography on flash silica using hexane and ethyl acetate (9:1) and precipitation from hexane and toluene (1:1) yielded 9.7 g (42%) of the title compound as a yellow solid (42%). 1H NMR (400 MHz, DMSO-d6) δ 8.36 (d, 1 H, J=2.0 Hz), 8.12 (d, 1 H, J=8.4 Hz), 7.44 (d, 1 H, J=2.4 Hz), 7.38 (d, 1 H, J=8.8 Hz), 2.59 (s, 3 H).

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux
  3. customto dry the resin
  4. temperaturerefluxing
  5. customreaction mixture under nitrogen over a 15 minute period
  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), then wash with 0.5M aqueous sodium hydroxide and aqueous saturated sodium chloride
  12. dry with materialDry over anhydrous magnesium sulfate
  13. filtrationfilter
  14. concentrationconcentrate under reduced pressure
  15. customhexane and ethyl acetate (9:1) and precipitation from hexane and toluene (1:1)

Sources & evidence

ORD record
ord-6618e59ee5754af196fc0334915697ab
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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