Ethyl Acetate → 4-Hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile

HRID 1405958Notes

Reaction equation

HRID 1405958 reaction equation
C[O:2][C:3]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-].CC(=O)OCC>C(Cl)Cl.Cl>[OH:2][C:3]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 867011894-Methoxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile

Product 1

HCID 867011884-Hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrileYield 56.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile (1.5 g) in anhydrous DCM (30 mL) was added anhydrous AlCl3 (6 g) at 0° C. The resulting mixture was heated to reflux for 1 h. After reaction finished, the mixture was diluted with 1N aqueous HCl (50 mL) and exacted with EA (3×50 mL). The combined organic layer was dried over Na2SO4, concentrated under reduced pressure, and purification by silica chromatography to give 0.8 g of 4-hydroxy-5-(2-methoxyethoxy)-2-nitrobenzonitrile.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customAfter reaction
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure, and purification by silica chromatography

Sources & evidence

ORD record
ord-4f22c70a0a4547c58edde51d35fd930a
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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