Ethylene Glycol → 3-(2-methyl-1,3-dioxolan-2-yl)aniline

HRID 1067719Notes

Reaction equation

HRID 1067719 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][C:2]1([C:4]2[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=2)[NH2:10])[O:13][CH2:12][CH2:11][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 74173'-Aminoacetophenone

Product 1

HCID 2929133-(2-methyl-1,3-dioxolan-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4 g (0.029 mol) of 3-aminoacetophenone and 2.47 ml (0.044 mol; 1.5 equivalents) of ethylene glycol and a small amount of 4-toluenesulphonic acid in 60 ml of anhydrous benzene are heated to reflux with azeotropic removal of water for 4 hours. The solution is left to cool, washed successively with 20% aqueous sodium carbonate and water and then dried (MgSO4). The solvent is evaporated off under reduced pressure to leave a yellow oil, which is purified by chromatography on a column of silica gel using a diethyl ether/petroleum ether (1:1) mixture as eluent, and then crystallized in hexane to yield 3-(2-methyl-1,3-dioxolan-2-yl)aniline, m.p. 75-77° C.

Workup

  1. waitThe solution is left
  2. temperatureto cool
  3. washwashed successively with 20% aqueous sodium carbonate and water
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated off under reduced pressure
  6. customto leave a yellow oil, which
  7. customis purified by chromatography on a column of silica gel using a diethyl ether/petroleum ether (1:1) mixture as eluent
  8. customcrystallized in hexane

Sources & evidence

ORD record
ord-a25309852bd44d4e9adb881c3d62629c
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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