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

HRID 1405963Notes

Reaction equation

HRID 1405963 reaction equation
C[O:2][C:3]1[C:4]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[C:8]#[N:9].[Al+3].[Cl-].[Cl-].[Cl-].CC(=O)OCC>C(Cl)Cl.Cl>[OH:2][C:3]1[C:4]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 115868825-Methoxy-4-(2-methoxyethoxy)-2-nitrobenzonitrile

Product 1

HCID 898856845-Hydroxy-4-(2-methoxyethoxy)-2-nitrobenzonitrileYield 35.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-4-(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 0.5 g of 5-hydroxy-4-(2-methoxyethoxy)-2-nitrobenzonitrile. 1H-NMR (400 MHz, CDCl3): δ: 7.85 (s, 1H), 7.33 (s, 1H), 4.32-4.30 (m, 2H), 3.87-3.84 (m, 2H), 3.50 (s, 3H).

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-1bd78ff471fb42a8b4a69ca8efd1366e
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

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