Ethylene Glycol → 1,4-Dioxaspiro[4.5]decane-7-carboxylic acid

HRID 1034194노트

반응식

HRID 1034194 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10]CC)=[O:9])[CH2:3]1.[CH2:13](O)[CH2:14][OH:15].[OH-].[Na+]>C1C=CC=CC=1.C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:1]1[C:2]2([CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]2)[O:15][CH2:14][CH2:13]1

참가 물질

8

반응물 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 118096Ethyl 3-oxocyclohexanecarboxylate

생성물 1

HCID 5674921,4-Dioxaspiro[4.5]decane-7-carboxylic acid

시약·촉매·용매 4

HCID 6101p-Toluenesulfonic acid촉매HCID 241Benzene용매HCID 702Ethanol용매HCID 962Water용매

실험 절차

A mixture of ethyl 3-oxocyclohexanecarboxylate (Nallet, J-P., et al, Bull. Soc. Chem. Fr., Part II, No. 3-4, pages 153-156 (1979)) (101.7 g) ethylene glycol (38.9 g) and para-toluenesulfonic acid (5.5 g) in 1000 mL of benzene is refluxed with a Dean-Stark trap for 4 hours. The solution is cooled, washed with 1N sodium hydroxide and brine, dried over magnesium sulfate, and evaporated in vacuo to give 113.1 g of a light oil which is dissolved in 1000 mL of ethanol, treated with sodium hydroxide (25.3 g) in 250 mL of water, and refluxed for 2.5 hours. The mixture is concentrated in vacuo, cooled in an ice bath, and acidified with ice-cold 1N aqueous hydrochloric acid solution to a pH of 2. The title compound is extracted with chloroform (2×500 mL), dried over magnesium sulfate, and concentrated in vacuo. The title compound (99.3 g) is obtained as a yellowish oil, which is determined to be 98% pure by gas chromatography and is carried on without further purification.

후처리

  1. temperatureThe solution is cooled
  2. washwashed with 1N sodium hydroxide and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give 113.1 g of a light oil which
  6. temperaturerefluxed for 2.5 hours
  7. concentrationThe mixture is concentrated in vacuo
  8. temperaturecooled in an ice bath
  9. extractionThe title compound is extracted with chloroform (2×500 mL)
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4e81a9866a1d4680adecd772f3d6537d
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05314896

반응 노트

불러오는 중…