Hydrochloric Acid → Methyl cyano(7-methoxy-1-naphthyl)acetate

HRID 2374725Notes

Reaction equation

HRID 2374725 reaction equation
[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.[H-].[Na+].[C:18](=O)([O:21]C)[O:19][CH3:20].Cl>O1CCCC1>[C:14]([CH:13]([C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)[C:18]([O:19][CH3:20])=[O:21])#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 112640682-(7-Methoxynaphthalen-1-yl)acetonitrile

Product 1

HCID 15149128Methyl cyano(7-methoxy-1-naphthyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7-Methoxy-naphth-1-yl)acetonitrile (20 g) is dissolved in 150 ml of anhydrous tetrahydrofuran. Sodium hydride (202.8 mmol) is added at ambient temperature, and the mixture is refluxed for 30 minutes. Dimethyl carbonate (12 ml) is added with caution, and the reaction mixture is refluxed for 30 minutes. The mixture is poured into ice-cold water, and the aqueous phase is acidified with 21 ml of 37% hydrochloric acid solution and then extracted twice with 100 ml of ether. The organic phase is washed with water, dried, decolored and evaporated. The oil obtained is precipitated from ether, and the precipitate formed is filtered off under suction and then recrystallized to yield the title product in the form of a white solid.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperaturethe reaction mixture is refluxed for 30 minutes
  3. additionThe mixture is poured into ice-cold water
  4. extractionextracted twice with 100 ml of ether
  5. washThe organic phase is washed with water
  6. customdried
  7. customevaporated
  8. customThe oil obtained
  9. customis precipitated from ether
  10. customthe precipitate formed
  11. filtrationis filtered off under suction
  12. customrecrystallized

Sources & evidence

ORD record
ord-8f2162168cf04176a7f7cb7ab192faa0
Source dataset
uspto-grants-2008_12
Patent number
US07462741B2

Reaction notes

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