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

HRID 1671748Notes

Reaction equation

HRID 1671748 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-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapour phase chromatography. When all the starting substrate has disappeared, the reaction mixture is cooled to ambient temperature and then filtered. After removal of the toluene by evaporation, the resulting solid residue is recrystallised from an ethanol/water (80/20) mixture to give the title product in a yield of 91% and with a chemical purity exceeding 99%.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. temperatureat reflux
  4. filtrationfiltered
  5. customAfter removal of the toluene
  6. customby evaporation
  7. customthe resulting solid residue is recrystallised from an ethanol/water (80/20) mixture

Sources & evidence

ORD record
ord-1388898b002748e38167e9d68428206d
Source dataset
uspto-grants-2011_08
Patent number
US07994359B2

Reaction notes

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