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

HRID 250524Notes

Reaction equation

HRID 250524 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].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][OH:26]>C1(C)C=CC=CC=1>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2]2([CH3:1])[O:26][CH2:25][CH2:24][O:3]2)=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 7487p-Nitroacetophenone

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-nitroacetophenone (1.65 g, 10.0 mmol), p-toluenesulfonic acid (172 mg, 1.00 mmol) and ethylene glycol (1.7 mL, 30 mmol) in dry toluene (20 mL) was heated at reflux with a Dean-Stark apparatus under nitrogen for 24 h. The mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. The residue was taken up in ether (20 mL) and the solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL), then dried (Na2SO4) and concentrated under reduced pressure. Recrystallisation from ether and hexanes afforded 2-(4-nitrophenyl)-2-methyl-1,3-dioxolane (25) as a pale yellow crystals (1.52 g, 73%; yield based from the first crop of crystals). 1H nmr (300 MHz, CDCl3) 1.66 (s, 3H, CH3), 3.71-3.83 (m, 2H, OCH2), 4.02-4.13 (m, 2H, OCH2), 7.63-7.73 (d, J=8.8 Hz, 2H, 2×ArH), 8.16-8.26 (d, J=8.8 Hz, 2H, 2×ArH).

Workup

  1. temperaturewas heated
  2. temperatureat reflux with a Dean-Stark apparatus under nitrogen for 24 h
  3. customthe solvent was evaporated in vacuo
  4. washthe solution was washed with saturated sodium bicarbonate solution (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallisation from ether and hexanes

Sources & evidence

ORD record
ord-ec1a1a81f3674d8fb3a1e464e58b4f23
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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