Hydrochloric Acid → HCID 12356700, compound

HRID 2256331Notes

Reaction equation

HRID 2256331 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.Cl.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH:29]=[CH2:30]>>[C:8]([C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:30][CH2:29][C:28]([O:32][CH2:33][CH3:34])=[O:31])#[N:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6837DiphenylacetonitrileHCID 8821Ethyl AcrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 12356700HCID 12356700, compound

Conditions

Temperature
80 °C

Procedure

To an ethanolic solution (100 ml) of diphenylacetonitrile (28 g) were added DBU (6 ml) and ethyl acrylate (30 ml) and the mixture was heated and stirred at 80° C. for 16 hours. After cooling, 200 ml of 2N-hydrochloric acid was added to the reaction mixture, which was then extracted with isopropyl ether. The organic layer was washed with water, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The resulting crude crystals were recrystallized from hexane/isopropyl ether to provide ethyl 4-cyano-4,4-diphenylbutyrate (34 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionwas then extracted with isopropyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude crystals were recrystallized from hexane/isopropyl ether

Sources & evidence

ORD record
ord-b9a137aff6074d2ba66a673a17ac968e
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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