Ethanol → 2-(Phenylmethyl)propanedinitrile

HRID 1587992Notes

Reaction equation

HRID 1587992 reaction equation
[N+]([C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+].C(O)C>C(OC(=O)C)C.O>[CH2:8]([CH:9]([C:10]#[N:11])[C:12]#[N:13])[C:7]1[CH:14]=[CH:15][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 20412-(4-(Hydroxy(oxido)amino)benzylidene)malononitrileHCID 4311764Sodium borohydride

Product 1

HCID 158462-(Phenylmethyl)propanedinitrileYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.5 Grams of 4-nitrobenzylidenemalononitrile, prepared according to Example 1, was dissolved in 200 milliliters of ethylacetate. To this was added an aqueous solution of 0.54 gram of sodium borohydride in 5 milliliters of water, and the mixture was stirred at ambient temperature for 1/2 hour. The organic layer was separated, using a separatory funnel, and washed three times with water. The organic extract was dried over anhydrous sodium sulfate, and evaporated to dryness. The crude reaction product was crstallized from ethanol to obtain 3.07 grams(67.5% yield) of the product. IR(nujol) analysis showed bands at 3100, 2950-2850, 2250, 1980, 1595, 1505, 1450, 1440, 1370, 1340, 1290, 1175, 1100, 1010, 885, 860, 845, 755 and 710 cm-1. NMR analysis (CDCl3) showed signals at 8.30 (d, 2H, J=7.8 Hz), 7.56 (d, 2H, J=7.8 Hz), 4.05 (t, 1H, J=6.3 Hz) and 3.42 (d, 2H, J=6.3 Hz) ppm. Elemental analysis: C10H7N3O2 requires: C=59.7; H=3.48; N=20.90%. Found: C=59.62; H=3.39; N=20.81%.

Workup

  1. customThe organic layer was separated
  2. washwashed three times with water
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe crude reaction product

Sources & evidence

ORD record
ord-c6fb7e588add4a97afc40ea0b7569a31
Source dataset
uspto-grants-1993_06
Patent number
US05220000

Reaction notes

Loading…