Sodium Cyanide → (4-Phenoxynaphthalen-1-yl)acetonitrile

HRID 1275422Notes

Reaction equation

HRID 1275422 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1>CS(C)=O>[C:1]([CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 22119575HCID 22119575, compound

Product 1

HCID 16736776(4-Phenoxynaphthalen-1-yl)acetonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium cyanide (3.7 g; 75 mMol) was dissolved in DMSO (50 mL, dried over molecular sieves). The mixture was heated in an oil bath maintained at 50° C., and 15.7 g (50 mMol) of 1-bromomethyl-4-phenoxynaphthalene, prepared as described above, in 75 mL of DMSO was added dropwise. After addition was complete, stirring was continued for 0.5 hours. The temperature was raised to 70° C., and stirring was continued for 1.0 hour. The oil bath was turned off, and the stirring was continued overnight. The mixture was poured onto ice, and extracted with ether. The combined organic extractions were washed with brine and dried over magnesium sulfate. The product was obtained as a white, crystalline solid (6.24 g; 49% yield). mass 259. A sample was purified for analysis by medium pressure chromatography on silica gel, eluting with ethyl acetate:hexane/1:9.

Workup

  1. temperatureThe mixture was heated in an oil bath
  2. additionwas added dropwise
  3. additionAfter addition
  4. temperatureThe temperature was raised to 70° C.
  5. stirringstirring
  6. waitwas continued for 1.0 hour
  7. waitthe stirring was continued overnight
  8. additionThe mixture was poured onto ice
  9. extractionextracted with ether
  10. extractionThe combined organic extractions
  11. washwere washed with brine
  12. dry with materialdried over magnesium sulfate
  13. customThe product was obtained as a white, crystalline solid (6.24 g; 49% yield)
  14. customA sample was purified for analysis by medium pressure chromatography on silica gel
  15. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-bcd05489d9a6498b9a41efe12a9cdefe
Source dataset
uspto-grants-2000_12
Patent number
US06160175

Reaction notes

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