Ethylene Glycol → 4-(2-Methyl-1,3-dioxolan-2-yl)butanenitrile

HRID 1044735Notes

Reaction equation

HRID 1044735 reaction equation
N#N.[O:3]=[C:4]([CH3:10])[CH2:5][CH2:6][CH2:7][C:8]#[N:9].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH3:10][C:4]1([CH2:5][CH2:6][CH2:7][C:8]#[N:9])[O:13][CH2:12][CH2:11][O:3]1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 947NitrogenHCID 6101p-Toluenesulfonic acidHCID 82611Hexanenitrile, 5-oxo-HCID 516892Sodium Bicarbonate

Product 1

HCID 155808174-(2-Methyl-1,3-dioxolan-2-yl)butanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus and under inert atmosphere (N2), 5-oxo-hexanenitrile (1.69 g, 15.2 mmol) was dissolved in dry toluene (10 mL). Ethylene glycol (4.24 mL, 76.0 mmol) and p-TsOH (289 mg, 1.5 mmol) were added and the reaction mixture stirred at 120° C. for 5 h. The reaction mixture was then cooled down to rt and sat. aq. NaHCO3 was added. The layers were separated and the aq. layer extracted with CH2Cl2 (2×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.94 min.

Workup

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. temperatureThe reaction mixture was then cooled down to rt
  3. customThe layers were separated
  4. extractionthe aq. layer extracted with CH2Cl2 (2×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53cd7a1372cf4f0084d2350ed3d61464
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

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