Propionitrile → HCID 547425, compound

HRID 1518175Notes

Reaction equation

HRID 1518175 reaction equation
[CH3:1][C:2]([CH3:10])=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11](#[N:14])[CH2:12][CH3:13].[OH-:15].[Na+]>O>[CH3:1][C:2]([NH:14][C:11](=[O:15])[CH2:12][CH3:13])([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7854PropionitrileHCID 13030(2-Methyl-1-propenyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 547425HCID 547425, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (2-methyl-propenyl)-benzene (2.6 g, 19.67 mmol) in propionitrile (20 g, 363 mmol) H2SO4 (39.33 mmol) was added at 10° C. The mixture was stirred at room temperature for 16 h. Then the mixture was poured into water and adjusted to an alkaline pH with NaOH. The aqueous layer was extracted three times with ethyl acetate, the organic layers combined, washed with water and brine, dried over MgSO4, filtered, and the solvent evaporated under reduced pressure to give the product as a yellow oil (1.6 g, 40%).

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-d71e59c9e2274bbc9da34355c0250b31
Source dataset
uspto-grants-2012_07
Patent number
US08232426B2

Reaction notes

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