Acrylonitrile → 7-METHOXY-2H-CHROMENE-3-CARBONITRILE

HRID 870382Notes

Reaction equation

HRID 870382 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.N12CCN(CC1)CC2.[C:20](#[N:23])[CH:21]=[CH2:22]>C(OCC)(=O)C>[CH3:11][O:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:21]([C:20]#[N:23])[CH2:22][O:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 122430247-METHOXY-2H-CHROMENE-3-CARBONITRILEYield 72.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-hydroxy-4-methoxy-benzaldehyde (10.0 g, 65.72 mmol) and DABCO (1,4-diazabicyclo[2.2.2]octane) (1.84 g, 16.43 mmol) was added acrylonitrile (17.44 g, 328.62 mmol). The reaction mixture was refluxed for 20 h. The reaction mixture was diluted with ethyl acetate and the resulting rheum was separated. The organic phase was washed with a 1 molar solution of NaOH and then with a 1 molar solution of HCl. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product (8.89 g, 72% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. customthe resulting rheum was separated
  3. washThe organic phase was washed with a 1 molar solution of NaOH
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-2ce3dce5884f47b4b22de3754c5dbe51
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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