Ethanol → 3-(3-Dimethoxymethyl-4-nitrophenoxy)-benzonitrile

HRID 2088838Notes

Reaction equation

HRID 2088838 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:10]([O-:13])([O-])=O.[K+].[K+].F[C:17]1[CH:18]=[CH:19][C:20]([N+:25]([O-:27])=[O:26])=[C:21]([CH:24]=1)[CH:22]=[O:23].[CH2:28](O)C>>[CH3:28][O:23][CH:22]([O:13][CH3:10])[C:21]1[CH:24]=[C:17]([CH:18]=[CH:19][C:20]=1[N+:25]([O-:27])=[O:26])[O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 5870905-Fluoro-2-nitrobenzaldehyde

Product 1

HCID 586250533-(3-Dimethoxymethyl-4-nitrophenoxy)-benzonitrile

Procedure

A mixture of 3-cyanophenol (0.38 mol) in ethanol (600 mL) was stirred at room temperature and K2CO3 (0.29 mol) was added. 5-fluoro-2-nitrobenzaldehyde (0.18 mol) was added, and the reaction mixture was stirred and refluxed for 4 hours. The solvent was evaporated, and the residue was stirred in water and extracted with CH2Cl2. The organic layer was separated, dried, filtered off and the solvent was evaporated. The residue was triturated under diisopropyl ether, and then the formed solids were filtered off and dried to yield the title compound.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperaturerefluxed for 4 hours
  3. customThe solvent was evaporated
  4. stirringthe residue was stirred in water
  5. extractionextracted with CH2Cl2
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered off
  9. customthe solvent was evaporated
  10. customThe residue was triturated under diisopropyl ether
  11. filtrationthe formed solids were filtered off
  12. customdried

Sources & evidence

ORD record
ord-b9850a6552754ec2a3566a5d283ef11b
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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