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

HRID 2115583Notes

Reaction equation

HRID 2115583 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, decoloured and evaporated. The oil obtained is precipitated from ether, and the precipitate formed is filtered off under suction and then recrystallised 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. customrecrystallised

Sources & evidence

ORD record
ord-c6960a8650a2456da950cd97b02dafbe
Source dataset
uspto-grants-2008_10
Patent number
US07435850B2

Reaction notes

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