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

HRID 1948589Notes

Reaction equation

HRID 1948589 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2].[CH2:16](O)[CH2:17][OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6]2([O:18][CH2:17][CH2:16][O:9]2)[CH2:7][CH2:8]1)#[N:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 912824-Oxo-1-phenylcyclohexanenitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-cyano-4-phenylcyclohexanone (5.97 g, 30 mmole) was taken up in toluene (200 ml) and ethylene glycol (4 ml, 71.6 mmole) was added. After addition of p-toluenesulfonic acid (86 mg, 0.5 mmole) the reaction mixture was heated to the boil in a water separator. The course of the reaction was followed by thin layer chromatography. After 20 hours no starting product could be detected any longer by thin layer chromatography. After cooling, the toluene solution was extracted by shaking with water (5×30 ml) and saturated aqueous NaCl solution (3×20 ml) and dried over Na2SO4. After removing the solvent on a rotary evaporator the desired ketal was obtained in a yield of 6.8 g (94%) as a white solid with a melting point of 108°-110° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe toluene solution was extracted
  3. dry with materialdried over Na2SO4
  4. customAfter removing the solvent
  5. customon a rotary evaporator the desired ketal
  6. customwas obtained in a yield of 6.8 g (94%) as a white solid with a melting point of 108°-110° C.

Sources & evidence

ORD record
ord-a7dfe7db984940fa92f90a0ec0b62a21
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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