Ethylene Glycol → 4-(2-Methyl-1,3-dioxolan-2-yl)aniline

HRID 1726219Notes

Reaction equation

HRID 1726219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:9][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[O:13][CH2:12][CH2:11][O:10]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 7468p-AminoacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 110739824-(2-Methyl-1,3-dioxolan-2-yl)anilineYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4′-aminoacetophenone (1.45 g, 10.7 mmol), ethylene glycol (2.00 g, 32.2 mmol), and p-TsOH.H2O (2.45 g, 12.9 mmol) in toluene (30 mL) were heated to reflux under a Dean-Stark trap for 3.5 h. Basic work-up and purification gave 4-(2-methyl-[1,3]dioxolan-2-yl)-phenylamine as colourless crystals (0.67 g, 35%).

Workup

  1. temperaturewere heated
  2. temperatureto reflux under a Dean-Stark trap for 3.5 h
  3. customBasic work-up and purification

Sources & evidence

ORD record
ord-ca4e05feae4a4357a534fb16c33f84a3
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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