Water → 3-Ethoxy-4-methylbenzonitrile

HRID 1294449Notes

Reaction equation

HRID 1294449 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([OH:12])[CH:6]=1)#[N:4].[CH2:13](I)[CH3:14].O>CN(C=O)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)#[N:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 177509203-Hydroxy-4-methylbenzonitrile

Product 1

HCID 224761033-Ethoxy-4-methylbenzonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a reaction vessel was charged sodium hydride (4.8 g, 0.12 mol) and N,N′-dimethylformamide (40 ml), and a solution obtained by dissolving 4-cyano-2-hydroxytoluene (14) (13.3 g, 0.1 mol) in N,N′-dimethylformamide (40 ml) in an ice bath was dropped on this, and the solution was stirred for 1.0 hour at room temperature. Subsequently, ethyl iodide (18.7 g, 0.12 mol) was dropped in an ice water, and the solution was stirred for 1.5 hours at room temperature. To the reaction liquid was added water and extracted with ethyl acetate, then, washed with saturated saline, dried, and the solvent was distilled off under reduced pressure, to obtain 4-cyano-2-ethoxytoluene (15) (16.1 g, yield from (14) is 99%).

Workup

  1. customa solution obtained
  2. additionwas dropped on this, and the solution
  3. stirringthe solution was stirred for 1.5 hours at room temperature
  4. customTo the reaction liquid
  5. extractionextracted with ethyl acetate
  6. washwashed with saturated saline
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e166f9d60fe54325a81eeb7ab68476a1
Source dataset
uspto-grants-2007_07
Patent number
US07241625B2

Reaction notes

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