Ethylene Glycol → 8-Phenyl-1,4-dioxaspiro[4.5]decane-8-carbonitrile

HRID 76926Notes

Reaction equation

HRID 76926 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[CH2:16](O)[CH2:17][OH:18].O>C1(C)C=CC=CC=1>[C:10]1([C:5]2([C:8]#[N:9])[CH2:4][CH2:3][C:2]3([O:18][CH2:17][CH2:16][O:1]3)[CH2:7][CH2:6]2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 912824-Oxo-1-phenylcyclohexanenitrile

Product 1

HCID 122302748-Phenyl-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound of step 2 (43.3 g, 217 mmol) and ethylene glycol (27.4 g, 435 mmol) were boiled in toluol (430 mL) with the addition of p-toluol sulphonic acid (1.87 g, 10.9 mmol) at a water separator for 3 h with reflux. After the reaction had ended, the mixture was cooled, washed with NaHCO3 solution and saturated NaCl solution, dried with Na2SO4 and concentrated to low volume in a vacuum.

Workup

  1. temperaturewith reflux
  2. temperaturethe mixture was cooled
  3. washwashed with NaHCO3 solution and saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to low volume in a vacuum

Sources & evidence

ORD record
ord-16b2910dc5ad4b0c922ddeaeaa3e2eeb
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

Loading…