Acrylonitrile → 3-(3-Methoxyphenyl)-2-propenenitrile

HRID 1156454Notes

Reaction equation

HRID 1156454 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=O.[C:12](#[N:15])[CH:13]=C.C(N(C(C)C)C(C)C)C>[Pd](Cl)Cl.C1(=O)CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH:6]=[CH:13][C:12]#[N:15]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 74374m-Anisoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 342413-(3-Methoxyphenyl)-2-propenenitrileYield 6.3%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 7967CyclohexanoneSolvent

Procedure

The procedure described in Example 1 is repeated, except that 17.05 g (0.1 mol) of 3-methoxybenzoyl chloride, 6.63 g (0.125 mol) of acrylonitrile, 12.96 g (0.1 mol) of ethyldiisopropylamine, 0.1773 g (0.001 mol) of palladium chloride and 50 ml of cyclohexanone, as the solvent, are used. After a reaction time of 13 hours at 120° C, 1 g (0.0063 mol) of 3-methoxycinnamonitrile are obtained, corresponding to a yield of 6.3% of theory; boiling point 159°-166° C./19×102Pa.

Sources & evidence

ORD record
ord-7bdfaa302e7b4774a0667bfb8f788cb8
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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