Water → 2-(2-Ethoxyphenyl)heptanenitrile

HRID 330302Notes

Reaction equation

HRID 330302 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][C:7]#[N:8])[CH3:2].Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].O>CS(C)=O.CCOCC>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH:6]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7]#[N:8])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 109771-ChloropentaneHCID 14798Sodium HydroxideHCID 1446322-Ethoxyphenylacetonitrile

Product 1

HCID 146993902-(2-Ethoxyphenyl)heptanenitrileYield 47.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A three neck 300 ml flask fitted with a reflux condenser, thermometer and dropping funnel was charged with 18.52 grams (0.15 moles) of commercially available 2-ethoxy benzylcyanide in 50 ml of dimethyl sulfoxide (DMSO). To the reaction was added 17.6 grams (0.165 moles, 1.1 ec.) of 1-chloropentane. While stirring at room temperature, 13.2 grams (0.165 moles) of 50% NaOH in 20 ml of DMSO was added over 20 minutes. A slight exotherm occurred and the reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC) indicated the reaction was 92% complete. The reaction was stirred for an additional 3 hours, then water was added followed by 200 ml of ether. After washing with acid and brine, the solvent was concentrated and gave an oil which was distilled under vacuum (160°-165° C. at 0.5 mm) and gave 15.82 grams (47.7% yield) of product.

Workup

  1. customA three neck 300 ml flask fitted with a reflux condenser
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours after which gas-liquid chromatoqraphy (GLC)
  3. stirringThe reaction was stirred for an additional 3 hours
  4. washAfter washing with acid and brine
  5. concentrationthe solvent was concentrated
  6. customgave an oil which
  7. distillationwas distilled under vacuum (160°-165° C. at 0.5 mm)

Sources & evidence

ORD record
ord-d969d0c05ac54f4e988d2585848262ab
Source dataset
uspto-grants-1990_01
Patent number
US04895865

Reaction notes

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