Ethylene Glycol → Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylate

HRID 849068노트

반응식

HRID 849068 반응식
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[CH2:13](O)[CH2:14][OH:15].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C1C=CC=CC=1>[O:15]1[C:11]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:4]([O:3][CH2:2][CH3:1])=[O:5])[O:12][CH2:13][CH2:14]1

참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

생성물 1

HCID 336004Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylate수율 99.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To ethyl 2-cyclohexanonecarboxylate (Aldrich, 169.5 g, 1.0 mol) and ethylene glycol (Sigma, 166.7 g, 2,7 mol) in benzene (1.5 L) was added pyridinium tosylate (50.2 g, 0.2 mol). The reaction was refluxed under a nitrogen atmosphere and the water generated was removed using a Dean-Stark trap. After cooling the reaction to room temperature, half of the benzene was removed under reduced pressure and the residue was washed with 25% aqueous NaHCO3, stripped of all solvent, dissolved in CH2Cl2, dried (Na2SO4), filtered, and again stripped of all solvent under reduced pressure to provide 213 g of the title material.

후처리

  1. temperatureThe reaction was refluxed under a nitrogen atmosphere
  2. customthe water generated was removed
  3. temperatureAfter cooling
  4. customthe reaction to room temperature
  5. customhalf of the benzene was removed under reduced pressure
  6. washthe residue was washed with 25% aqueous NaHCO3
  7. dissolutiondissolved in CH2Cl2
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-629e2ab03a9a43f9b8e36c022221eab2
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011028

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