Sodium Carbonate → HCID 9120345, compound

HRID 1361017Notes

Reaction equation

HRID 1361017 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].[C:12]1([C:18]2[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[I-].[K+]>[C:18]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=[CH:20][C:21]([CH2:22][O:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[CH:24][CH:25]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 133943-CyanophenolHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 9120345HCID 9120345, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyanophenol (5.0 g, 40.72 mmol) in dry N,N-dimethylformamide (100 mL) kept under an atmosphere of nitrogen, sodium hydride (2 g, 48.86 mmol, 60% dispersion in oil) was added in portions and the reaction mixture was stirred until gas evolution ceased. p-Phenylbenzyl chloride (9.26 g, 44.79 mmol) and potassium iodide (0.2 g, 1.21 mmol) were added and the reaction mixture was stirred at room temperature for 60 hours. The reaction mixture was poured on to a mixture of saturated sodium carbonate (100 mL) and ice water (300 mL). The precipitate was filtered of and washed with water (3×100 mL), n-hexane (2×80 mL) and dried in vacuo at 50° C. for 18 hours affording 11.34 g (98%) of 3-(biphenyl-4-ylmethoxy)-benzonitrile as a solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 60 hours
  2. filtrationThe precipitate was filtered of and
  3. washwashed with water (3×100 mL), n-hexane (2×80 mL)
  4. customdried in vacuo at 50° C. for 18 hours

Sources & evidence

ORD record
ord-aab0c976efcc4eb6a860980b714e63a2
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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