Sodium hydride → 4,4'-[Oxybis(methylene)]dibenzonitrile

HRID 325059Notes

Reaction equation

HRID 325059 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[C:13]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)#[N:14]>C1COCC1>[CH2:19]([C:18]1[CH:21]=[CH:22][C:15]([C:13]#[N:14])=[CH:16][CH:17]=1)[O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 869964-(Bromomethyl)benzonitrileHCID 160549p-Cyanobenzyl alcohol

Product 1

HCID 131179744,4'-[Oxybis(methylene)]dibenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 4-cyanobenzyl alcohol (637 mg, 4.8 mmol) in dry THF (15 mL) was added a dispersion of sodium hydride in mineral oil (60%; 192 mg, 4.8 mmol), portionwise over five minutes under an argon atmosphere. The resulting milky white solution was allowed to warm to room temperature and stirred for three hours (bubbling was observed). To the resulting light green mixture was added dry dimethylformamide (3 mL) to improve homogeneity. After stirring for an additional hour, the 4-cyanobenzyl bromide (930 mg, 4.8 mmol) was added. The resulting yellow, cloudy mixture was stirred at room temperature overnight. The reaction was then carefully quenched with the addition of 1 N aqueous HCl (15 mL) and extracted with ether (3×30 mL). The combined ethereal extracts were washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo to provide the desired ether as a light yellow solid (1.06 g, 89%). No further purification was necessary.

Workup

  1. temperatureto warm to room temperature
  2. custom(bubbling was observed)
  3. additionTo the resulting light green mixture was added dry dimethylformamide (3 mL)
  4. stirringAfter stirring for an additional hour
  5. stirringThe resulting yellow, cloudy mixture was stirred at room temperature overnight
  6. customThe reaction was then carefully quenched with the addition of 1 N aqueous HCl (15 mL)
  7. extractionextracted with ether (3×30 mL)
  8. washThe combined ethereal extracts were washed with water and brine
  9. dry with materialthen dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto provide the desired ether as a light yellow solid (1.06 g, 89%)
  13. customNo further purification

Sources & evidence

ORD record
ord-4a0933a206404fe0af991886f6afa34c
Source dataset
uspto-grants-2001_04
Patent number
US06221914B1

Reaction notes

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