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

HRID 1948589
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HRID 1948589 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-a7dfe7db984940fa92f90a0ec0b62a21
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399503B2

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