Ethylene Glycol → HCID 23123916, compound

HRID 350844Notes

Reaction equation

HRID 350844 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])=[N+:2]=[N-:3].[CH2:15](O)[CH2:16][OH:17].O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:15]1[CH2:16][O:17][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[O:8]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 108779184-Azidobutyrophenone

Product 1

HCID 23123916HCID 23123916, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

4-Azidobutyrophenone (100.0 mg, 0.53 mmol) was dissolved in toluene (5 ml) at room temperature, and thereto were added ethylene glycol (0.06 ml, 1.06 mmol) and p-toluene sulfonic acid mono hydrate (10.1 mg, 0.05 mmol) in sequential order at the same temperature, and thereafter, the mixture was refluxed using a Dean Stark tube for 24 hours. The reaction solution was cooled to room temperature and added to water thereafter, followed by the extraction using ethyl acetate. The extracted organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The target compound was thus obtained as a colorless oil (133 mg).

Workup

  1. temperaturethe mixture was refluxed
  2. customfor 24 hours
  3. extractionfollowed by the extraction
  4. washThe extracted organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4bd8393f3aa4337a97d4be62cac3aaa
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

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