Ethylene Glycol → 2-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

HRID 450058Notes

Reaction equation

HRID 450058 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[O:15][CH2:14][CH2:13][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 7487p-Nitroacetophenone

Product 1

HCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolaneYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-nitro acetophenone (3 g, 18.18 mmol), ethylene glycol (1.35 g, 21.81 mmol) and p-toluene sulfonic acid (0.62 g) were taken in toluene and heated to reflux using a Dean-Stark water separator, until no more water was collected. The reaction mixture was cooled, water was added and the toluene layer separated. The aqueous layer was washed again with toluene and the toluene washings combined, dried and evaporated under reduced pressure to give 2-methyl-2-(4-nitro-phenyl)-[1,3]dioxolane (2.7 g, 71%) as oil.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customwas collected
  4. temperatureThe reaction mixture was cooled
  5. additionwater was added
  6. customthe toluene layer separated
  7. washThe aqueous layer was washed again with toluene
  8. customdried
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b8f029030f084d3b947ad6ceb29450e1
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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