Cesium carbonate → HCID 16577665, compound

HRID 706416Notes

Reaction equation

HRID 706416 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-].[Cs+].[Cs+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>C(#N)C>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 16577665HCID 16577665, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-hydroxy-3-methoxybenzonitrile (2.43 g, 16.29 mmol) in acetonitrile (75 mL) was added cesium carbonate (6.68 g, 20.50 mmol) and p-methoxybenzyl chloride (2.81 g, 17.92 mmol). The reaction mixture was heated to reflux and stirred. After 1 h, the mixture was allowed to cool to room temperature and was filtered. The filtrate was concentrated to provide 4.56 g (>100%) 3-methoxy-4-((4-methoxybenzyl)oxy)benzonitrile as an off-white solid. The crude material was used without purification in the next reaction.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5477b7cae5d94054add3959a4fcc8eee
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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