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

HRID 1941880Notes

Reaction equation

HRID 1941880 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[CH2:11](O)[CH2:12][OH:13].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:2]1[CH2:11][CH2:12][O:13][CH:1]1[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 660424-Cyanobenzaldehyde

Product 1

HCID 27784284-(1,3-Dioxolan-2-yl)benzonitrileYield 89.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-formylbenzonitrile (10 g, 76.3 mmol), ethylene glycol (18.95 g, 305 mmol) and p-toluene sulfonic acid (7 mg, 0.003 mmol) in toluene (100 mL) was heated to reflux for 9 hours. During this time a Dean-Stark trap was used to remove water formed during the reaction. To the reaction was added aq. Na2CO3 (150 mL). The organic layer was washed twice with water (100 mL), then dried over Na2SO4. The solvent was removed under vacuum to provide 4-(1,3-dioxolan-2-yl)benzonitrile (12 g, 68 mmol). The compound had an HPLC retention time=4.24 min. −Column: HYPERSIL® BDS C18 (4.6×50 mm) Flow rate=0.8 mL/min. Solvent A=, 0.1% TFA in water; Solvent B=acetonitrile. 5%-100% B (0-6 min), 100% B (6-9 min), 100%-5% B (9-11 min).

Workup

  1. temperatureto reflux for 9 hours
  2. customto remove water
  3. customformed during the reaction
  4. washThe organic layer was washed twice with water (100 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-d67eaa6d0ac248029084e07407b75991
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

Loading…