Pyridine → HCID 66625115, compound

HRID 417360Notes

Reaction equation

HRID 417360 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][OH:8].N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23]>C1COCC1>[C:22]([O:8][CH2:7][CH2:6][O:5][C:4]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=1[O:2][CH3:1])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 18368290HCID 18368290, compound

Product 1

HCID 66625115HCID 66625115, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-methoxy-4-nitrophenoxy)ethanol (5.5 g, 26 mmol) and pyridine (2.35 g, 30 mmol) in THF (140 mL) at 0° C. was acetyl chloride (2.33 g, 30 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The combined organic extract was washed with water, saturated aqueous CuSO4 solution, brine, dried over MgSO4, and concentrated to give 2-(2-methoxy-4-nitrophenoxy)ethyl acetate as a yellow solid (6 g, 91%).

Workup

  1. customat 0° C.
  2. concentrationThe mixture was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted with ethyl acetate
  6. extractionThe combined organic extract
  7. washwas washed with water, saturated aqueous CuSO4 solution, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-194b3211c0ff427c97d299af3e5775be
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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