Benzyl Chloride → 4-Benzyloxy-3-methoxy-benzonitrile

HRID 1072412Notes

Reaction equation

HRID 1072412 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 7937714-Benzyloxy-3-methoxy-benzonitrileYield 88.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 4-hydroxy-3-methoxybenzonitrile (20.0 g, 134 mmol) in acetone (200 ml) were added K2CO3 (55.6 g, 402 mmol) and benzyl chloride (23.2 ml, 201 mmol). The resulting reaction mixture was refluxed overnight. After cooling to room temperature, acetone was removed by evaporation under reduced pressure and the residue was recrystallized to obtain 4-benzyloxy-3-methoxy-benzonitrile(28.5 g, 88%). Then, according to the similar procedure of Example 1, 7-(4-Benzyloxy-3-methoxy-phenyl)-5-ethylsulfanyl-imidazo[1,2-c]pyrimidine was prepared.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customacetone was removed by evaporation under reduced pressure
  4. customthe residue was recrystallized

Sources & evidence

ORD record
ord-3a7adb79b0ed4d3c9ff73eb4e56fd08e
Source dataset
uspto-grants-2005_06
Patent number
US06911443B2

Reaction notes

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