Ethylene Glycol → HCID 23441498, compound

HRID 2119422Notes

Reaction equation

HRID 2119422 reaction equation
[C:1]([C:4]1([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[CH3:2][C:1]1([C:4]2([C:7]3[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=3)[CH2:6][CH2:5]2)[O:18][CH2:17][CH2:16][O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 23441476HCID 23441476, compound

Product 1

HCID 23441498HCID 23441498, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4-(1-acetylcyclopropan-1-yl)nitrobenzene (2.40 g), ethylene glycol (6.5 mL), and pyridinium p-toluenesulfonate (1.47 g) in benzene (120 mL) was heated under reflux with Dean-Stark apparatus for 15 hours. After cooling, dilution with saturated sodium hydrogencarbonate solution, the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=4:1) of the residue gave 4-(1-(2-methyl-1,3-dioxolan-2-yl)cyclopropan-1-yl)nitrobenzene (2.83 g).

Workup

  1. temperatureunder reflux with Dean-Stark apparatus for 15 hours
  2. temperatureAfter cooling
  3. extractiondilution with saturated sodium hydrogencarbonate solution, the mixture was extracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19f9d6592bc44261b5e51549ee410b24
Source dataset
uspto-grants-2004_02
Patent number
US06686363B2

Reaction notes

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