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

HRID 1087194Notes

Reaction equation

HRID 1087194 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:14](O)[CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2([CH3:12])[O:16][CH2:15][CH2:14][O:13]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanone

Product 1

HCID 100374432-(3-Chloro-4-nitrophenyl)-2-methyl-1,3-dioxolaneYield 106.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3'-chloro-4'-nitroacetophenone (3 g), ethylene glycol (9.3 g), and p-toluenesulfonic acid monohydrate (0.5 g) in toluene (30 ml) was refluxed for 6 hours. Water formed in the reaction was removed by means of Dean Stark apparatus. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate, and concentrated to give an oil of 2-(3-chloro-4-nitrophenyl)-2-methyl-1,3-dioxolane (3.9 g).

Workup

  1. customwas removed by means of Dean Stark apparatus
  2. washThe reaction mixture was washed with an aqueous solution of sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-935a3af827f3481e9370e71a95cf18c4
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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