Diethyl Ether → 4-(1-Methylpropoxy)phenoxyacetonitrile

HRID 2248189Notes

Reaction equation

HRID 2248189 reaction equation
[H-].[Na+].[CH3:3][CH:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH2:5][CH3:6].Cl[CH2:16][C:17]#[N:18].CCOCC>CN(C=O)C>[CH3:3][CH:4]([O:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:16][C:17]#[N:18])=[CH:12][CH:13]=1)[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 138820044-(1-Methyl-1-propyloxy)-phenol

Product 1

HCID 156625734-(1-Methylpropoxy)phenoxyacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To prewashed sodium hydride (1.01 g, 42.0 mmol) in 60 ml of DMF at 20° is added 4-(1-methylpropoxy)phenol (7.0 g, 42.0 mmol) in 5 ml of DMF over 30 min. After 1 hour at RT, chloroacetonitrile (3.80 g, 50.4 mmol) in 5 ml of DMF is added dropwise to the mixture at 5°-8° over 15 min. After addition, the reaction is warmed slowly to RT and stirred at RT for 18 hours. The mixture is then poured into ice water and ether and extracted with ether (3X). The combined organic phases are washed with 10% NaOH, with water until neutral and with brine, dried, filtered and solvent removed in vacuo to give 4-(1-methylpropoxy)phenoxyacetonitrile.

Workup

  1. additionAfter addition
  2. extractionextracted with ether (3X)
  3. washThe combined organic phases are washed with 10% NaOH, with water until neutral and with brine
  4. customdried
  5. filtrationfiltered
  6. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-96dedba34fc348f7ac663a208c1df64e
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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