Ethylene Glycol → HCID 67378455, compound

HRID 927851Notes

Reaction equation

HRID 927851 reaction equation
C[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1)=[O:3].[CH2:12]([OH:15])[CH2:13]O.B(F)(F)F.[C:20](=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.O>[O:15]1[CH2:12][CH2:13][O:3][CH:2]1[C:4]1([CH3:20])[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][CH2:9]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 6356Boron trifluorideHCID 740444'-CyanoacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 67378455HCID 67378455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-Cyanoacetophenone (5.0 g, 34.4 mmol) was dissolved in toluene (50 mL), had ethylene glycol (3.4 g, 55.1 mmol) and BF3 etherate (0.5 mL) added to it dropwise, was heated on a water separator for 12 h under reflux, allowed to cool to room temperature (yellow reaction solution), had a 5-percent sodium hydrogencarbonate solution (40 mL) added, was extracted with diethyl ether, washed with saturated sodium chloride solution (30 mL), dried over MgSO4, filtered, evaporated under vacuum, and recrystallized from diethyl ether/n-pentane (1:1), Yield: 2.2 g (34%) colorless solid, m.p. 70° C. 1H-NMR (200 MHz, CDCl3, 25° C.): δ=1.62 (s, 3 H, CH3), 3.72-3.75 (m, 2 H, CH2), 4.02-4.08 (m, 2 H, CH2), 7.57-7.64 ppm (m, 4 H, Haryl). HRMS (C11H12NO2): calc. m/z: 190.086, obs. m/z: 190.087, Δ=1 mmu.

Workup

  1. additionadded to it dropwise
  2. temperatureunder reflux
  3. additionadded
  4. extractionwas extracted with diethyl ether
  5. washwashed with saturated sodium chloride solution (30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customrecrystallized from diethyl ether/n-pentane (1:1), Yield: 2.2 g (34%) colorless solid, m.p. 70° C

Sources & evidence

ORD record
ord-0d753677e1004a9e891d7524fdf49c8f
Source dataset
uspto-grants-2016_03
Patent number
US09290494B2

Reaction notes

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