Water → 2-(3-Phenoxyphenyl)propanenitrile

HRID 1759430Notes

Reaction equation

HRID 1759430 reaction equation
C1(C)C=CC(S[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)([CH3:11])[C:9]#[N:10])=CC=1.O.CCOCC>C(O)(=O)C.[Zn].S([O-])([O-])(=O)=O.[Cu+2]>[O:18]([C:14]1[CH:13]=[C:12]([CH:8]([CH3:11])[C:9]#[N:10])[CH:17]=[CH:16][CH:15]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 13023169alpha-(p-Tolylthio)-alpha-(m-phenoxyphenyl)propionitrile

Product 1

HCID 1180062-(3-Phenoxyphenyl)propanenitrileYield 92%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent

Procedure

417 mg of alpha-(p-tolylthio)-alpha-(m-phenoxyphenyl)propionitrile was dissolved in 4 ml of acetic acid. Zinc powder (370 mg) and 25 mg of anhydrous copper sulfate were added. The mixture was heated under reflux for 1 hour with stirring. After the cooling, 20 ml of water and 20 ml of ether were added. The insoluble matter was separated by filtration. Sodium carbonate (5 g) was added to the filtrate to neutralize the acetic acid, followed by extraction with ether (15 ml×4 times). The extract was washed with 30 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel; hexane and methylene chloride) to afford 247 mg (yield 92%) of alpha-(m-phenoxyphenyl)propionitrile as an oil. A sample for elemental analysis was prepared by subjecting the oil to bulb-to-bulb distillation [149°-154° C. (bath temperature)/1 torr].

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe insoluble matter was separated by filtration
  4. additionSodium carbonate (5 g) was added to the filtrate
  5. extractionfollowed by extraction with ether (15 ml×4 times)
  6. washThe extract was washed with 30 ml of water three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe oily residue was purified by column chromatography (silica gel; hexane and methylene chloride)

Sources & evidence

ORD record
ord-30b651f40c3540449793385ac86587d4
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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