Ethylene Glycol → 4-(1,3-Dioxolan-2-yl)benzonitrile

HRID 735986Notes

Reaction equation

HRID 735986 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH2:11](O)[CH2:12][OH:13].O>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:11][CH2:12][O:13][CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 660424-Cyanobenzaldehyde

Product 1

HCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileYield 51.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-cyanobenzaldehyde (25 g, 0.190 mol) in dry toluene (300 mL) was added ethyleneglycol (15 g, 0.228 mol) and PTSA (0.5 g) and allowed to reflux at 130° C. with azeotropic removal of water for 12 h. The reaction mixture was cooled, washed with 10% aqueous NaHCO3 (100 mL), dried and concentrated under vacuum. The crude solid was recrystallised from PetEther/EtOAc to give the 4-(1,3-dioxolan-2-yl)benzonitrile (17 g, 51%) as white solid. TLC (PetEther/EtOAc 4/1), Rf=0.6

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 10% aqueous NaHCO3 (100 mL)
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe crude solid was recrystallised from PetEther/EtOAc

Sources & evidence

ORD record
ord-540ba33213644cd489051e9f831fc97a
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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