Ethyl Acetate → HCID 22168204, compound

HRID 1031661Notes

Reaction equation

HRID 1031661 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27](Cl)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[C:26]([N+:31]([O-:33])=[O:32])[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 90154-MethoxyphenolHCID 110436225-Benzyloxy-2-chloro-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22168204HCID 22168204, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

880 mg of 4-methoxyphenol was dissolved in 10 ml of N,N-dimethylformamide. 790 mg of potassium t-butoxide was added thereto. Then, 1.7 g of 4-benzyloxy-2-nitro-chlorobenzene was added thereto. The mixture was stirred for 1 hour at 110°-120° C. The reaction mixture was introduced into a mixture of 50 ml of ice water and 50 ml of ethyl acetate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: toluene) to obtain 1.92 g of 5-benzyloxy-2-(4-methoxyphenoxy)nitrobenzene.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by a column chromatography (eluant: toluene)

Sources & evidence

ORD record
ord-79568ce28e274197955a28217b65eee3
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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