Acrylonitrile → 2H-1-Benzopyran-3-carbonitrile, 6-methoxy-

HRID 428164Notes

Reaction equation

HRID 428164 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.N12CCN(CC1)CC2.[C:20](#[N:23])[CH:21]=[CH2:22]>C(Cl)(Cl)Cl>[CH3:11][O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:22][C:21]([C:20]#[N:23])=[CH:4]2

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 956952-Hydroxy-5-methoxybenzaldehyde

Product 1

HCID 424402H-1-Benzopyran-3-carbonitrile, 6-methoxy-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 0.61 g (4 mmol) of 2-hydroxy-5-methoxybenzaldehyde and 0.112 g (1 mmol) of 1,4-diazabicyclo[2.2.2]octane in 18 ml of acrylonitrile is heated at reflux for 24 hours under argon. After cooling, the medium is diluted with chloroform and then washed with a saturated solution of sodium hydrogen carbonate. The organic phase is then acidified with a hydrochloric acid solution (1N); the aqueous phase is then extracted with chloroform. The organic phases, dried over magnesium sulphate and then filtered, are concentrated under reduced pressure. The title nitrile is obtained pure in the form of a yellow solid after passage over a silica column (eluant:AcOEt/PE:25/75).

Workup

  1. temperatureat reflux for 24 hours under argon
  2. temperatureAfter cooling
  3. washwashed with a saturated solution of sodium hydrogen carbonate
  4. extractionthe aqueous phase is then extracted with chloroform
  5. dry with materialThe organic phases, dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-e02f653cabba47cea4e473e598f7ad81
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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