6-Methoxy-alpha-tetralone → 1-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-

HRID 847244Notes

Reaction equation

HRID 847244 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.C[Si]([C:18]#[N:19])(C)C.[Al+3].[Cl-].[Cl-].[Cl-]>[Zn+2].[I-].[I-].C1C=CC=CC=1>[C:18]([C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH:8]=1)#[N:19]

Participants

6

Reactant 3

HCID 141126-Methoxy-alpha-tetraloneHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 30144661-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-Yield 94%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 241BenzeneSolvent

Procedure

To a refluxing benzene solution (60 ml) of 6-methoxy-1-tetralone was added trimethylsilyl cyanide (TMSCN) (67.5 g) and a trace of AlCl3 or ZnI2. Refluxing was continued for 1 hr., then the solvent removed under vacuum. Isopropyl alcohol saturated with HCl(g) was added and the solution refluxed for 1 hr. Precipitation began to occur and the reaction was cooled, then evaporated to dryness. Water was added, followed by an ethyl acetate (EtOAc) extraction. The organic layer was washed in sequence with 1 N NaOH, IN HCl, and brine, separated, dried (MgSO4), filtered and evaporated. The dark oil was chromatographed on silica gel and eluted with CH2Cl2, affording 98.5 g, 94% yield of product.

Workup

  1. temperatureRefluxing
  2. custom, then the solvent removed under vacuum
  3. additionIsopropyl alcohol saturated with HCl(g) was added
  4. temperaturethe solution refluxed for 1 hr
  5. customPrecipitation
  6. temperaturethe reaction was cooled
  7. customevaporated to dryness
  8. additionWater was added
  9. extractionfollowed by an ethyl acetate (EtOAc) extraction
  10. washThe organic layer was washed in sequence with 1 N NaOH, IN HCl
  11. custombrine, separated
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customevaporated
  15. customThe dark oil was chromatographed on silica gel
  16. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-6e41bdef3f4e4d1da54201246046bc13
Source dataset
uspto-grants-1992_08
Patent number
US05140040

Reaction notes

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