Allyl methacrylate → 2-(7-Methoxynaphthalen-1-yl)acetonitrile

HRID 2193967Notes

Reaction equation

HRID 2193967 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1.C(OCC=C)(=O)C(C)=C>C1(C)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]#[N:15])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7274Allyl methacrylateHCID 11287102(7-Methoxy-3,4-dihydronaphthalen-1-yl)acetonitrile

Product 1

HCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile dissolved in toluene are added and also 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is monitored by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After evaporating off the toluene, the solid residue obtained is recrystallised from an ethanol/water (80/20) mixture to yield the title product in a yield of 91% and with a chemical purity of more than 99%.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. additionare added
  4. temperatureat reflux
  5. filtrationfiltered
  6. customAfter evaporating off the toluene
  7. customthe solid residue obtained
  8. customis recrystallised from an ethanol/water (80/20) mixture

Sources & evidence

ORD record
ord-918a03f61a584ab5add799d355bee453
Source dataset
uspto-grants-2012_12
Patent number
US08329947B2

Reaction notes

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