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

HRID 2070109Notes

Reaction equation

HRID 2070109 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](O)[CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:9][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[O:16][CH2:15][CH2:14][O:10]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 1387234-Hydroxy-3-NitroacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 190269674-(2-Methyl-1,3-dioxolan-2-yl)-2-nitrophenol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred mixture of 1-(4-hydroxy-3-nitrophenyl)ethanone (3.00 g, 16.56 mmol), ethylene glycol (1.385 mL, 24.84 mmol) and p-toluenesulfonic acid monohydrate (0.158 g, 0.828 mmol) in toluene (60 mL) was heated to reflux for 18 hr in a 250 mL round bottom flask fitted with a Dean-Stark apparatus. The mixture was cooled and diluted with EtOAc (80 mL) and then washed with water (3×30 mL) and brine (20 mL), dried (Na2SO4) and concentrated to dryness in vacuo to afford a thick brown oily residue. This was purified by silica gel chromatography eluting with 5-50% Et2O in isohexane. The title product was isolated as a yellow oil (2.41 g, 64.6%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hr in a 250 mL round bottom flask
  3. customfitted with a Dean-Stark apparatus
  4. temperatureThe mixture was cooled
  5. washwashed with water (3×30 mL) and brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to dryness in vacuo
  8. customto afford a thick brown oily residue
  9. customThis was purified by silica gel chromatography
  10. washeluting with 5-50% Et2O in isohexane

Sources & evidence

ORD record
ord-306a026bb2ed4134acc43d3feaec2827
Source dataset
uspto-grants-2012_10
Patent number
US08299257B2

Reaction notes

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