Ethylene Glycol → HCID 57585844, compound

HRID 547614Notes

Reaction equation

HRID 547614 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:31](O)[CH2:32][OH:33]>C1(C)C=CC=CC=1.C(OC(=O)C)C>[CH3:1][C:2]1[CH:3]=[C:4]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]3[O:33][CH2:32][CH2:31][O:17]3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 54893623HCID 54893623, compound

Product 1

HCID 57585844HCID 57585844, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(3-Methyl-4-nitrophenyl)oxy]benzaldehyde (1.72 g, 6.4 mmol), p-toluenesulfonic acid (120 mg, 0.64 mmol), and ethylene glycol (1.7 mL, 32 mmol) were heated to reflux in 70 mL toluene for 16 hours in a round bottom flask equipped with a Dean-Stark trap. The reaction mixture was cooled to room temperature, diluted with ethylacetate and extracted with 1N NaOH. The organic layer was dried over MgSO4, filtered and concentrated to afford 1.89 g crude 2-{4-[(3-methyl-4-nitrophenyl)oxy]phenyl}-1,3-dioxolane, which was used without further purification.

Workup

  1. customequipped with a Dean-Stark trap
  2. extractionextracted with 1N NaOH
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6b25e328e115489c94f3db431219f7be
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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