Ethylene Glycol → HCID 11333948, compound

HRID 1393967Notes

Reaction equation

HRID 1393967 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH2:16](O)[CH2:17][OH:18]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:17]1[O:18][C:12]2([CH2:13][CH2:14][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)=[CH:10][CH2:11]2)[O:15][CH2:16]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 11275622HCID 11275622, compound

Product 1

HCID 11333948HCID 11333948, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

4-(3-cyanophenyl)-3-cyclohexene-1-one (from step 1 of method 2, 1.8 g, 9.0 mmole), ethylene glycol (2.8 g, 45 mmole) and p-toluenesulfonic acid monohydrate (0.1 g, 0.5 mmole) were dissolved in 50 ml toluene. The reaction was refluxed for 2 hours. The organic layer was washed with water (2×50 mL) and dried over sodium sulfate. The residue from the organic layer was purified by column chromatography using ethyl acetate/hexane (15/85) as the eluent to afford 4-(3-cyanophenyl)-3-cyclohexene-1-one ethylene ketal(1.9 g, 87%).

Workup

  1. temperatureThe reaction was refluxed for 2 hours
  2. washThe organic layer was washed with water (2×50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe residue from the organic layer was purified by column chromatography

Sources & evidence

ORD record
ord-44614f8b72ce403eafd77a1515c181e6
Source dataset
uspto-grants-2008_03
Patent number
US07348328B2

Reaction notes

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