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

HRID 1921676Notes

Reaction equation

HRID 1921676 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 962WaterHCID 6101p-Toluenesulfonic acidHCID 7487p-Nitroacetophenone

Product 1

HCID 6065982-Methyl-2-(4-nitrophenyl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

33.03 g (200 mmol) of 4-nitroacetophenone, 12.30 mL (220 mmol) of ethylene glycol, and 1.00 g (5 mmol) of p-toluenesulfonic acid are placed in 250 mL of toluene, then refluxed for 16 hours using the water separator. Then the reaction mixture is cooled and extracted with water. The organic phase is dried and evaporated to dryness. The residue is extracted with diisopropyl ether and suction filtered. Yield: 34.45 g (82%).

Workup

  1. temperaturerefluxed for 16 hours
  2. temperatureThen the reaction mixture is cooled
  3. extractionextracted with water
  4. customThe organic phase is dried
  5. customevaporated to dryness
  6. extractionThe residue is extracted with diisopropyl ether and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-30b27a052385492885953219544c1036
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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