Potassium Carbonate → 3-(3-Dimethoxymethyl-4-nitrophenoxy)-benzonitrile

HRID 390216Notes

Reaction equation

HRID 390216 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([CH:26]([O:29][CH3:30])[O:27][CH3:28])[CH:18]=1>CN(C)C(=O)C>[CH3:30][O:29][CH:26]([O:27][CH3:28])[C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[N+:23]([O-:25])=[O:24])[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3-hydroxybenzonitrile (0.129 mol) in N,N-dimethyl-acetamide (200 mL) was stirred at room temperature and K2CO3 (0.147 mol) was added, then 4-chloro-2-dimethoxymethyl-1-nitrobenzene (0.086 mol) was added and the reaction mixture was stirred for 24 hours at 130° C. The solvent was evaporated and the residue was stirred in H2O. After extraction with CH2Cl2, the organic layer was separated, dried, filtered off and the solvent was evaporated. The residue was purified over a silica gel filter (eluent: CH2Cl2 100%). The purest product fractions were collected and the solvent was evaporated to yield the title compound as residue.

Workup

  1. stirringthe reaction mixture was stirred for 24 hours at 130° C
  2. customThe solvent was evaporated
  3. stirringthe residue was stirred in H2O
  4. extractionAfter extraction with CH2Cl2
  5. customthe organic layer was separated
  6. customdried
  7. filtrationfiltered off
  8. customthe solvent was evaporated
  9. customThe residue was purified over a silica gel
  10. filtrationfilter (eluent: CH2Cl2 100%)
  11. customThe purest product fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f7f19d62fa4b4b389669ca46c93597e6
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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