Methanol → 2-(1-Naphthyl)-2-(methoxycarbonyl)acetonitrile

HRID 37286

Reaction equation

HRID 37286 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na].CO.[C:17](=O)([O:20]C)[O:18][CH3:19]>>[C:1]1([CH:11]([C:17]([O:18][CH3:19])=[O:20])[C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 85961-NaphthaleneacetonitrileHCID 12021Dimethyl CarbonateHCID 5360545Sodium

Product 1

HCID 108468152-(1-Naphthyl)-2-(methoxycarbonyl)acetonitrile

Procedure

0.1 mol of 2-(1-naphthyl)acetonitrile is dissolved in 120 cm3 of dimethyl carbonate, and the solution is heated to reflux. 0.1 mol of sodium is then added in small portions over 30 min, during which time the methanol evaporates off. The reaction medium is kept refluxing for 1 hour, and the excess dimethyl carbonate is then evaporated off to dryness. The residue is taken up with 100 cm3 of an 18% solution of acetic acid in water.

Workup

  1. temperaturethe solution is heated to reflux
  2. customevaporates off
  3. temperatureThe reaction medium is kept refluxing for 1 hour
  4. customthe excess dimethyl carbonate is then evaporated off to dryness

Sources & evidence

ORD record
ord-87392b3e925043f0acdd97a4f40532ee
Source dataset
uspto-grants-1995_05
Patent number
US05420158

Linked notes

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